Catalytic enantioselective sulfinyl transfer using cinchona alkaloid catalysts
Catalytic enantioselective sulfinyl transfer using cinchona alkaloid catalysts
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DOI：
10.1021/ol050275p
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发表时间：
2005-04-28
期刊：
影响因子：
5.2
通讯作者：
Ellman, JA
中科院分区：
文献类型：
--
作者：
Peltier, HM;Evans, JW;Ellman, JA
报道了催化不对称合成亚磺酸酯的实际反应条件。市售的金鸡纳生物碱被发现是叔丁基亚磺酰氯和各种苄醇的亚磺酰基转移反应的上级催化剂。用2，4，6-三氯苄醇和10mol%的市售廉价催化剂奎尼丁进行亚磺酰基转移反应，得到纯的亚磺酸酯产物，分离产率为92%，ee为90%。
Practical reaction conditions for the catalytic enantioselective synthesis of sulfinate esters are reported. Commercially available cinchona alkaloids were found to be superior catalysts for the sulfinyl transfer reaction of tert-butanesulfinyl chloride and a variety of benzyl alcohols. Sulfinyl transfer with 2,4,6-trichlorobenzyl alcohol and 10mol% of the commercially available, inexpensive catalyst quinidine provided the pure sulfinate ester product in 92% isolated yield and with 90% ee.