Journal
TETRAHEDRON-ASYMMETRY
Volume 22, Issue 7, Pages 713-716Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2011.04.022
Keywords
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Funding
- NSF [CHE0616154, CHE0911638]
- NIH [RR15569]
- Arkansas Biosciences Institute
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Epoxy quinol la was prepared on a multi-gram scale by Noyori transfer hydrogenative desymmetrization of the readily available meso-epoxy diketone 4. Although the intrinsic enantioselectivity for the desymmetrization was modest (82:18 er at 4% conversion), a highly enantiopure product (99.6:0.4 er) could be obtained in one operation in 44% yield via kinetic resolution of the minor enantiomer with long reaction times (48 h), or in 73% yield by combination with an enzymatic resolution of a 93:7 er mixture. (C) 2011 Elsevier Ltd. All rights reserved.
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