One-pot asymmetric synthesis of acyclic chiral epoxy alcohols via tandem vinylation-epoxidation with dioxygen
AE Lurain, PJ Carroll, PJ Walsh
Index: Lurain, Alice E.; Carroll, Patrick J.; Walsh, Patrick J. Journal of Organic Chemistry, 2005 , vol. 70, # 4 p. 1262 - 1268
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Abstract
We have developed a one-pot procedure for the asymmetric synthesis of a synthetically challenging class of acylic secondary epoxy alcohols with three contiguous stereocenters from simple achiral starting materials. The epoxy alcohols are synthesized via a tandem catalytic asymmetric vinylation of an aldehyde coupled with a diastereoselective epoxidation reaction. A vinylzinc reagent generated in situ undergoes enantioselective addition to an ...
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