Hansch Markus, Illa Ona, McGarrigle Eoghan M, Aggarwal Varinder K
School of Chemistry, University of Bristol, Cantock's Close, UK.
Chem Asian J. 2008 Sep 1;3(8-9):1657-63. doi: 10.1002/asia.200800174.
Chiral nonracemic thiomorpholines have been synthesized in four to six steps from limonene or achiral alkenes using alpha-methylbenzylamine to control absolute stereochemistry. These aminosulfides have been used to generate sulfur ylides, which have been applied in the asymmetric epoxidation of aldehydes as easily recoverable catalysts. Excellent yields (up to 98 %), enantioselectivities (up to 97:3 e.r.), and diastereoselectivities (>or=98:2 trans/cis) were achieved in these epoxidations and the sulfides were easily recovered in high yield (up to 97 %) by simple acid/base extraction.
手性非外消旋硫代吗啉已通过四至六步反应，从柠檬烯或非手性烯烃出发，使用α-甲基苄胺来控制绝对立体化学而合成。这些氨基硫化物已被用于生成硫叶立德，后者已作为易于回收的催化剂应用于醛的不对称环氧化反应中。在这些环氧化反应中实现了优异的产率（高达98%）、对映选择性（高达97:3的对映体比例）和非对映选择性（≥98:2的反式/顺式比例），并且通过简单的酸碱萃取可轻松地以高产率（高达97%）回收硫化物。
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