Stereoselective Conjugate Addition of Organolithium Reagents to Enoates Derived from Glyceraldehyde Acetonide
- 1 January 1990
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1990 (10) , 613-614
- https://doi.org/10.1055/s-1990-21185
Abstract
Alkyllithium reagents react preferentially 1,4 and in a highly syn stereoselective manner with γ-alkoxy enoates (alkyl 4,5-isopropylidenedioxy-2-pentenoates) derived from glyceraldehyde acetonide (2,3-isopropylidenedioxy-1-propanal), to provide synthetically useful chiral building blocks. We suggest a transition-state model for such additions based on MM2 calculations.Keywords
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