Asymmetric Synthesis of γ‑Lactones through Koga Amine-Controlled Addition of Enediolates to α,β-Unsaturated Sulfoxonium Salts

A chiral Koga amine-controlled asymmetric synthesis of cis-γ-lactones through a formal [3 + 2] cycloaddition of enediolates with α,β-unsaturated sulfoxonium salts is described. The desired structural motif was formed in moderate to good yields (50–71% for 13 examples), with good to very good diaster...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2017-01, Vol.82 (1), p.606-615
Main Authors: Peraino, Nicholas J, Kaster, Sven H, Wheeler, Kraig A, Kerrigan, Nessan J
Format: Article
Language:English
Subjects:
Acetates - chemistry
Amines - chemistry
Cycloaddition Reaction
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Salts - chemistry
Stereoisomerism
Sulfonium Compounds - chemistry
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 chiral Koga amine-controlled asymmetric synthesis of cis-γ-lactones through a formal [3 + 2] cycloaddition of enediolates with α,β-unsaturated sulfoxonium salts is described. The desired structural motif was formed in moderate to good yields (50–71% for 13 examples), with good to very good diastereoselectivity (dr 5:1 to 10:1 for 20 examples), favoring the cis-isomer, and good to excellent enantioselectivity (70–91% ee for 13 examples).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02622