Stereoselective synthesis of fused vinylcyclopropanes by intramolecular TsujiTrost cascade cyclization

A stereoselective intramolecular TsujiTrost cascade cyclization of (homo)allylic vicinal diacetates with a pendant β-ketoamide or related carbon nucleophile to give γ-lactam-fused vinylcyclopropanes is reported. In addition to two new rings, the products contain three new CC stereocenters (two of which are quaternary) with a 9:1 dr. Moreover, the reaction proceeds in >94% enantiospecificity with optically enriched starting materials, using an inexpensive carbohydrate as the source of chirality.

Publication year:2018

Keywords:A1 Journal article

BOF-keylabel:yes

BOF-publication weight:10

CSS-citation score:2

Authors:International

Authors from:Higher Education

Accessibility:Open