N‑Heterocyclic Carbene-Catalyzed Ireland–Coates Claisen Rearrangement: Synthesis of Functionalized β‑Lactones

N‑Heterocyclic Carbene-Catalyzed Ireland–Coates Claisen Rearrangement: Synthesis of Functionalized β‑Lactones

The N-heterocyclic carbene (NHC)-catalyzed Claisen rearrangement of hybrid Ireland–Coates structures has been achieved, allowing the stereoselective synthesis of highly functionalized β-lactones. The reaction proceeds with high diastereoselectivity (>20:1) and affords a diverse range of β-lactone...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2013-01, Vol.135 (1), p.58-61
Main Authors: Candish, Lisa, Lupton, David W
Format: Article
Language:eng
Subjects:
Catalysis
Heterocyclic Compounds - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Stereoisomerism
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The N-heterocyclic carbene (NHC)-catalyzed Claisen rearrangement of hybrid Ireland–Coates structures has been achieved, allowing the stereoselective synthesis of highly functionalized β-lactones. The reaction proceeds with high diastereoselectivity (>20:1) and affords a diverse range of β-lactone fused cyclopentanes. Mechanistic studies are detailed.
ISSN:0002-7863
1520-5126