Synthesis and application of easily recyclable thiomorpholines for use in sulfur ylide mediated asymmetric epoxidation of aldehydes
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 alde...
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Published in | Chemistry, an Asian journal Vol. 3; no. 8-9; p. 1657 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Germany
01.09.2008
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Online Access | Get more information |
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Summary: | 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. |
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ISSN: | 1861-471X |
DOI: | 10.1002/asia.200800174 |