Enantioselective Allylation of β,γ-Unsaturated Aldehydes Generated via Lewis Acid Induced Rearrangement of 2-Vinyloxiranes
- 15 December 2001
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (1) , 83-86
- https://doi.org/10.1021/ol016946a
Abstract
[reaction: see text] 2-Vinyloxiranes have been found to be excellent surrogates to beta,gamma-unsaturated aldehydes. These valuable electrophiles, generated in situ by treatment of a 2-vinyloxirane with a catalytic amount of Sc(OTf)(3), are effectively trapped by the chiral allylating agents based on alpha-pinene, affording bishomoallylic alcohols in high yield and excellent selectivity.Keywords
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