Enantioselective γ‑Alkylation of α,β-Unsaturated Malonates and Ketoesters by a Sequential Ir-Catalyzed Asymmetric Allylic Alkylation/Cope Rearrangement

A catalytic, enantioselective γ-alkylation of α,β-unsaturated malonates and ketoesters is reported. This strategy entails a highly regio- and enantioselective iridium-catalyzed α-alkylation of an extended enolate, and a subsequent translocation of chirality to the γ-position via a Cope rearrangement...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2016-04, Vol.138 (16), p.5234-5237
Main Authors: Liu, Wen-Bo, Okamoto, Noriko, Alexy, Eric J, Hong, Allen Y, Tran, Kristy, Stoltz, Brian M
Format: Article
Language:English
Subjects:
Alkylation
Allyl Compounds - chemistry
Catalysis
Crystallography, X-Ray
Esters - chemistry
Iridium
Magnetic Resonance Spectroscopy
Malonates - chemistry
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A catalytic, enantioselective γ-alkylation of α,β-unsaturated malonates and ketoesters is reported. This strategy entails a highly regio- and enantioselective iridium-catalyzed α-alkylation of an extended enolate, and a subsequent translocation of chirality to the γ-position via a Cope rearrangement.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b02153