Affordable Access

deepdyve-link deepdyve-link
Publisher Website

Intermolecular asymmetric carboesterification of alkenes by using chiral amine auxiliaries under O2: synthesis of enantioenriched α-methylene-γ-lactones through chloropalladation of alkynes.

Authors
Type
Published Article
Journal
Chemistry - A European Journal
1521-3765
Publisher
Wiley Blackwell (John Wiley & Sons)
Publication Date
Volume
21
Issue
18
Pages
6708–6712
Identifiers
DOI: 10.1002/chem.201500397
PMID: 25760781
Source
Medline
Keywords
License
Unknown

Abstract

Herein, the first example of chloropalladation-initiated asymmetric intermolecular carboesterification of alkenes with alkynes by using chiral amine auxiliaries is reported. The use of (1S,2S)-N(1),N(1)-dimethylcyclohexane-1,2-diamine auxiliaries is essential for providing α-methylene-γ-lactones products in moderate to high yields and excellent enantioselectivities at room temperature. Moreover, the chiral amine auxiliaries can be readily removed by hydrolysis during the reaction process to keep the absolute configuration. This oxygen- and water-promoted asymmetric reaction opens a new window to study asymmetric processes in halopalladation reactions.

Statistics

Seen <100 times