S-叔丁基-β-(三氟甲基)异半胱氨酸的非对映选择性合成。
Diastereoselective synthesis of S-tert-butyl-beta-(trifluoromethyl)isocysteine.
作者信息
Ohkura Hironari, Handa Michiharu, Katagiri Toshimasa, Uneyama Kenji
机构信息
Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700-8530, Japan.
出版信息
J Org Chem. 2002 Apr 19;67(8):2692-5. doi: 10.1021/jo016108u.
Both diastereoisomers of S-tert-butyl-beta-(trifluoromethyl)isocysteine have been synthesized stereoselectively by the sequential reactions of trifluoroacetimidoyl chloride with the lithium enolate of tert-butyl alpha-tert-butylthioacetate, followed by the diastereoselective reduction of the imino group with sodium borohydride in the presence of zinc(II) or di(ethylene glycol) dimethyl ether, and finally by the deprotection of N-aryl and tert-butyl ester groups.
通过三氟乙酰亚胺酰氯与叔丁基α-叔丁基硫代乙酸酯的烯醇锂依次反应，然后在锌（II）或二（乙二醇）二甲醚存在下用硼氢化钠非对映选择性还原亚氨基，最后脱除N-芳基和叔丁基酯基，立体选择性地合成了S-叔丁基-β-（三氟甲基）异半胱氨酸的两种非对映异构体。
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