{"id":3603,"date":"2015-02-12T20:10:47","date_gmt":"2015-02-12T12:10:47","guid":{"rendered":"\/\/www.gsbet888.com\/?p=3603"},"modified":"2019-08-02T18:55:54","modified_gmt":"2019-08-02T10:55:54","slug":"%e5%ae%89%e5%be%b7%e6%a3%ae%e6%89%8b%e6%80%a7%e4%ba%9a%e7%a0%9c%e5%90%88%e6%88%90%e6%b3%95andersen-chiral-sulfoxide-synthesis","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/%e5%8f%96%e4%bb%a3%e5%8f%8d%e5%ba%94\/2015\/02\/%e5%ae%89%e5%be%b7%e6%a3%ae%e6%89%8b%e6%80%a7%e4%ba%9a%e7%a0%9c%e5%90%88%e6%88%90%e6%b3%95andersen-chiral-sulfoxide-synthesis.html","title":{"rendered":"\u5b89\u5fb7\u68ee\u624b\u6027\u4e9a\u781c\u5408\u6210\u6cd5(Andersen Chiral Sulfoxide Synthesis)"},"content":{"rendered":"<ul>\n<li><strong>\u6982\u8981<\/strong><\/li>\n<\/ul>\n<div class=\"boxed\">\n<div class=\"content\">\n<div class=\"wrapper\">\n<div class=\"main-content-left\">\n<div class=\"main-article-content\">\n<div class=\"shortcode-content\">\n<p>\u8584\u8377\u4e9a\u781c\u5728\u70f7\u57fa\u9502\u6216\u8005Grignard\u8bd5\u5242\u7684\u4f5c\u7528\u4e0b\uff0c\u5f97\u5230\u624b\u6027\u4e9a\u781c\u7684\u5408\u6210\u624b\u6cd5\u3002<\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u57fa\u672c\u6587\u732e<\/strong><\/li>\n<\/ul>\n<div class=\"boxed\">\n<div class=\"content\">\n<div class=\"wrapper\">\n<div class=\"main-content-left\">\n<div class=\"main-article-content\">\n<div class=\"shortcode-content\">\n[1]. Gilman, H.; Robinson, J.; Beaber, N. J. <em>J. Am. Chem. Soc.<\/em> <strong>1926<\/strong>, 48 , 2715.\u00a0DOI: <a class=\"ext-link ext-icon-2\" title=\"\" href=\"http:\/\/dx.doi.org\/10.1021\/ja01421a030\" rel=\"external\" data-wpel-target=\"_blank\">10.1021\/ja01421a030<\/a><\/p>\n[2]. Andersen, K. K. <em>Tetrahedron Lett.<\/em> <strong>1962<\/strong> , 3, 93.\u00a0doi:<a class=\"ext-link ext-icon-2\" title=\"\" href=\"http:\/\/dx.doi.org\/10.1016\/S0040-4039(00)71106-3\" rel=\"external\" data-wpel-target=\"_blank\">10.1016\/S0040-4039(00)71106-3<\/a><\/p>\n[3]. Andersen, K. K.; Gaffield, W.; Papanikolaou, N. E.; Foley, J. W.; Perkins, R. I. <em>J. Am. Chem. Soc<\/em>. <strong>1964<\/strong> , <em>86<\/em> , 5637. DOI:\u00a0<a class=\"ext-link ext-icon-2\" title=\"\" href=\"http:\/\/dx.doi.org\/10.1021\/ja01078a047\" rel=\"external\" data-wpel-target=\"_blank\">10.1021\/ja01078a047<\/a><\/p>\n[4]. Andersen, K. K.; Bujnicki, B.; Drabowicz,J.; Mikolajczyk, M.; O\u2019Brien, J. B. <em>J. Org. Chem.<\/em><strong>1984<\/strong>, <em>49<\/em>, 4070. DOI: <a class=\"ext-link ext-icon-2\" title=\"\" href=\"http:\/\/dx.doi.org\/10.1021\/jo00195a042\" rel=\"external\" data-wpel-target=\"_blank\">10.1021\/jo00195a042<\/a><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u5f00\u53d1\u5386\u53f2<\/strong><\/li>\n<\/ul>\n<div class=\"boxed\">\n<div class=\"content\">\n<div class=\"wrapper\">\n<div class=\"main-content-left\">\n<div class=\"main-article-content\">\n<div class=\"shortcode-content\">\n<p>Andersen\u7b49\u4eba\u4eceGilman\u5f00\u53d1\u7684\u78fa\u9178\u76d0\u7684Grignard\u8bd5\u5242\u7684\u52a0\u6210\u53cd\u5e94\u4e2d\u5f97\u5230\u542f\u53d1,\u57281962\u5e74\u7528\u8584\u8377\u9187\u4e0e\u7532\u82ef\u78fa\u9170\u6c2f\u53cd\u5e94\u5f97\u5230\u8584\u8377\u4e9a\u781c\uff0c\u7ecf\u91cd\u7ed3\u6676\u540e\u5f97\u5230\u5149\u5b66\u7eaf\u7684\u4ea7\u7269\u3002\u7136\u540e\u518d\u4e0eGrignard\u8bd5\u5242\u53cd\u5e94\uff0c\u6210\u529f\u5408\u6210\u4e86\u5177\u6709\u5149\u5b66\u6d3b\u6027\u7684\u4e9a\u781c\u3002<\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53cd\u5e94\u673a\u7406<\/strong><\/li>\n<\/ul>\n<div class=\"boxed\">\n<div class=\"content\">\n<div class=\"wrapper\">\n<div class=\"main-content-left\">\n<div class=\"main-article-content\">\n<div class=\"shortcode-content\">\n<p>\u901a\u8fc7\u4eb2\u6838\u53d6\u4ee3\u5f97\u5230\u7acb\u4f53\u7ffb\u8f6c\u7684\u4ea7\u7269\u3002<\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2015\/01\/anders7.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-3604 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2015\/01\/anders7.gif\" alt=\"anders7\" width=\"362\" height=\"94\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53cd\u5e94\u5b9e\u4f8b<\/strong><\/li>\n<\/ul>\n<div class=\"boxed\">\n<div class=\"content\">\n<div class=\"wrapper\">\n<div class=\"main-content-left\">\n<div class=\"main-article-content\">\n<div class=\"shortcode-content\">\n<p>Ethyl Deoxymonate B\u7684\u5408\u6210[1]\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2015\/01\/andersen_s_3.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-3605 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2015\/01\/andersen_s_3.gif\" alt=\"andersen_s_3\" width=\"467\" height=\"78\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u5b9e\u9a8c\u6b65\u9aa4<\/strong><\/li>\n<\/ul>\n<div class=\"boxed\">\n<div class=\"content\">\n<div class=\"wrapper\">\n<div class=\"main-content-left\">\n<div class=\"main-article-content\">\n<div class=\"shortcode-content\">\n<p>\u914d\u4f4d\u5b50sox\u7684\u5408\u6210[2]\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2015\/01\/2014-08-29_03-18-21.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-3606 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2015\/01\/2014-08-29_03-18-21.png\" alt=\"2014-08-29_03-18-21\" width=\"595\" height=\"219\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2015\/01\/2014-08-29_03-18-21.png 595w, https:\/\/assets.www.gsbet888.com\/uploads\/2015\/01\/2014-08-29_03-18-21-300x110.png 300w\" sizes=\"(max-width: 595px) 100vw, 595px\" \/><\/a><\/p>\n<div class=\"boxed\">\n<div class=\"content\">\n<div class=\"wrapper\">\n<div class=\"main-content-left\">\n<div class=\"main-article-content\">\n<div class=\"shortcode-content\">\n<p>\u5728\u6c2e\u6c14\u4fdd\u62a4\uff0c\u00a0\u201378 \u02daC \u6761\u4ef6\u4e0b\u3001 \u5f80(<em>S<\/em>)-2-(2-bromophenyl)-4-isopropyl-4,5-dihydrooxazole\u00a0(678 mg, 3.0 mmol)\u7684THF\u6eb6\u6db2 (15 mL) \u4e2d\u7f13\u6162\u52a0\u5165\u00a0<em>n<\/em>-BuLi (1.6 M in hexane, 2.1 mL, 3.3 mmol)\u3002 \u5728\u201378 \u02daC\u6405\u62cc\u4e00\u5c0f\u65f6\u540e\uff0c \u518d\u52a0\u5165(1<em>R<\/em>,2<em>S<\/em>,5<em>R<\/em>)-(-)-menthyl (<em>S<\/em>)-<em>p<\/em>-toluenesulfinate (971 mg, 3.3 mmol) \u7684THF \u6eb6\u6db2(15 m L)\u3001 \u5e76\u4e14\u7ee7\u7eed\u5728\u201378 \u02daC\u6405\u62cc30\u5206\u540e\u3001\u5347\u9ad8\u5230\u5ba4\u6e29\u518d\u6405\u62cc30\u5206\u949f\u3002\u6405\u62cc\u5b8c\u6210\u540e\u3001\u52a0\u5165\u9971\u548c\u6c2f\u5316\u94f5\u6c34\u6eb6\u6db2\u3001\u5e76\u4e14\u7528\u4e59\u9178\u4e59\u916f\u8403\u53d6\u3002\u6709\u673a\u76f8\u7528\u9971\u548c\u98df\u76d0\u6c34\u6d17\u51c0\u3001\u518d\u7528\u65e0\u6c34\u786b\u9178\u94a0\u5e72\u71e5\u3001\u8fc7\u6ee4\u3001\u51cf\u538b\u84b8\u998f\u9664\u53bb\u6eb6\u5242\u3002\u7c97\u4ea7\u7269\u901a\u8fc7\u8fc7\u67f1\u5b50 (hexane\/EtOAc = 3:1)\u7cbe\u5236\u7eaf\u5316\u3001\u5f97\u5230\u767d\u8272\u56fa\u4f53\u72b6\u7684\u76ee\u6807\u4ea7\u7269<strong>sox\u3002<\/strong><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u5b9e\u9a8c\u6280\u5de7<\/strong><\/li>\n<\/ul>\n<div class=\"boxed\">\n<div class=\"content\">\n<div class=\"wrapper\">\n<div class=\"main-content-left\">\n<div class=\"main-article-content\">\n<div class=\"shortcode-content\">\n<p>\u203b\u5bf9\u4e8e\u5408\u6210\u624b\u6027\u4e9a\u781c\u5316\u5408\u7269\uff0c\u8fd8\u6709\u522b\u7684\u4e00\u4e9b\u65b9\u6cd5\u6bd4\u5982<a class=\"ext-link ext-icon-2\" title=\"\" href=\"http:\/\/www.chem-station.com\/odos\/2009\/06\/sharplesssharpless-katsukiasym.html\" rel=\"external\" data-wpel-target=\"_blank\">Sharpless-\u9999\u6708\u4e0d\u5bf9\u79f0<\/a>\u73af\u6c27\u5316\u7b49\u3002\u4f46\u662f\uff0c\u901a\u8fc7\u4e0d\u5bf9\u79f0\u7b97\u8bdd\u5f97\u5230\u7684\u4e9a\u781c\u4ea7\u7269\u901a\u4ea7\u5149\u5b66\u7eaf\u5ea6\u8fbe\u4e0d\u5230&gt;99%ee\u3001\u56e0\u6b64\uff0c\u5230\u73b0\u5728\u4f4d\u7f6e\uff0c\u5b89\u5fb7\u68ee\u7684\u8fd9\u4e2a\u624b\u6027\u4e9a\u781c\u5408\u6210\u7684\u624b\u6cd5\u8fd8\u5728\u88ab\u5e7f\u6cdb\u7684\u4f7f\u7528\u3002<\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53c2\u8003\u6587\u732e<\/strong><\/li>\n<\/ul>\n<div class=\"boxed\">\n<div class=\"content\">\n<div class=\"wrapper\">\n<div class=\"main-content-left\">\n<div class=\"main-article-content\">\n<div class=\"shortcode-content\">[1] de la Pradilla, R. F.; Lwoff, N. <em>Tetrahedron Lett.<\/em> <strong>2008<\/strong>,\u00a0<em>49<\/em>, 4167. doi:<a class=\"ext-link ext-icon-2\" title=\"\" href=\"http:\/\/dx.doi.org\/10.1016\/j.tetlet.2008.04.107\" rel=\"external\" data-wpel-target=\"_blank\">10.1016\/j.tetlet.2008.04.107<\/a> [2]\u00a0Yamaguchi, K.; Kondo, H.; Yamaguchi, J.; Itami, K. <em>Chem. Sci.<\/em> <strong>2013<\/strong>, 4, 3753\u00a0DOI: <a class=\"ext-link ext-icon-2\" title=\"\" href=\"http:\/\/dx.doi.org\/10.1039\/C3SC51206A\" rel=\"external\" data-wpel-target=\"_blank\">10.1039\/C3SC51206A\u00a0<\/a><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n","protected":false},"excerpt":{"rendered":"\u6982\u8981 \u8584\u8377\u4e9a\u781c\u5728\u70f7\u57fa\u9502\u6216\u8005Grignard\u8bd5\u5242\u7684\u4f5c\u7528\u4e0b\uff0c\u5f97\u5230\u624b\u6027\u4e9a\u781c\u7684\u5408\u6210\u624b\u6cd5\u3002 &nbsp; \u57fa\u672c\u6587\u732e [1]. Gilman, H.; Robinson, J.; Beaber, N. J. J. Am. Chem. Soc. 1926, 48 , 2715.\u00a0DOI: 10.1021\/ja01421a030 [2]. Andersen, K. K. Tetrahedron Lett. 1962 , 3, 93.\u00a0doi:10.1016\/S0040-4039(00)71106-3 [3]. Andersen, K. K.; Gaffield, W.; Papanikolaou, N. E.; Foley, J. W.; Perkins, R. I. J. Am. Chem. Soc. 1964 , 86 , 5637. DOI:\u00a010.1021\/ja01078a047 [4]. Andersen, K. K.; Bujnicki, B.; Drabowicz,J.; Mikolajczyk, M.; O\u2019Brien, J. B. J. Org. Chem.1984, 49, 4070. DOI: 10.1021\/jo00195a042 &nbsp; \u5f00\u53d1\u5386\u53f2 Andersen\u7b49\u4eba\u4eceGilman\u5f00\u53d1\u7684\u78fa\u9178\u76d0\u7684Grignard\u8bd5\u5242\u7684\u52a0\u6210\u53cd\u5e94\u4e2d\u5f97\u5230\u542f\u53d1,\u57281962\u5e74\u7528\u8584\u8377\u9187\u4e0e\u7532\u82ef\u78fa\u9170\u6c2f\u53cd\u5e94\u5f97\u5230\u8584\u8377\u4e9a\u781c\uff0c\u7ecf\u91cd\u7ed3\u6676\u540e\u5f97\u5230\u5149\u5b66\u7eaf\u7684\u4ea7\u7269\u3002\u7136\u540e\u518d\u4e0eGrignard\u8bd5\u5242\u53cd\u5e94\uff0c\u6210\u529f\u5408\u6210\u4e86\u5177\u6709\u5149\u5b66\u6d3b\u6027\u7684\u4e9a\u781c\u3002 &nbsp; \u53cd\u5e94\u673a\u7406 \u901a\u8fc7\u4eb2\u6838\u53d6\u4ee3\u5f97\u5230\u7acb\u4f53\u7ffb\u8f6c\u7684\u4ea7\u7269\u3002 &nbsp; \u53cd\u5e94\u5b9e\u4f8b Ethyl Deoxymonate B\u7684\u5408\u6210[1] &nbsp; \u5b9e\u9a8c\u6b65\u9aa4 \u914d\u4f4d\u5b50sox\u7684\u5408\u6210[2] \u5728\u6c2e\u6c14\u4fdd\u62a4\uff0c\u00a0\u201378 \u02daC \u6761\u4ef6\u4e0b\u3001 \u5f80(S)-2-(2-bromophenyl)-4-isopropyl-4,5-dihydrooxazole\u00a0(678 mg, 3.0 mmol)\u7684THF\u6eb6\u6db2 (15 mL) \u4e2d\u7f13\u6162\u52a0\u5165\u00a0n-BuLi (1.6 M in hexane, 2.1 mL, 3.3 mmol)\u3002 \u5728\u201378 \u02daC\u6405\u62cc\u4e00\u5c0f\u65f6\u540e\uff0c \u518d\u52a0\u5165(1R,2S,5R)-(-)-menthyl [&hellip;]","protected":false},"author":5,"featured_media":3727,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"jetpack_post_was_ever_published":false,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","enabled":false},"version":2}},"categories":[16],"tags":[325,688],"jetpack_publicize_connections":[],"jetpack_featured_media_url":"https:\/\/assets.www.gsbet888.com\/uploads\/2015\/02\/2014-08-29_02-43-37.png","jetpack_shortlink":"https:\/\/wp.me\/p96op1-W7","jetpack_sharing_enabled":true,"_links":{"self":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/3603"}],"collection":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/users\/5"}],"replies":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/comments?post=3603"}],"version-history":[{"count":2,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/3603\/revisions"}],"predecessor-version":[{"id":28000,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/3603\/revisions\/28000"}],"wp:featuredmedia":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/media\/3727"}],"wp:attachment":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/media?parent=3603"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/categories?post=3603"},{"taxonomy":"post_tag","embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/tags?post=3603"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}