Stereoselective allylation of chiral monoperoxyacetals

Authors

Aqeel Ahmed, University of Nebraska - Lincoln
Patrick Dussault, University of Nebraska-LincolnFollow

Document Type

Article

Date of this Version

May 2005

Comments

Published in Tetrahedron 61:19 (9 May 2005), pp. 4657–4670. Copyright © 2005 Elsevier Ltd. Used by permission. doi:10.1016/j.tet.2005.02.071 http://www.sciencedirect.com/science/journal/00404020

Abstract

Neighboring iodo-, alkoxy-, acetoxy- and silyl groups impart useful levels of diastereoselection in the Lewis acid-mediated allylation of monoperoxyacetals. Although monoperoxyacetals are found to be considerably less reactive than corresponding nonperoxidic acetals, similar stereochemical trends are observed in the two series.