Issue 6, 2017

Aerobic oxidation and EATA-based highly enantioselective synthesis of lamenallenic acid

Abstract

By utilizing the recently developed EATA (enantioselective allenylation of terminal alkynes) reaction and the aerobic oxidation of alcohols, lamenallenic acid, a naturally occurring axially chiral allene, has been synthesized with a high ee value and E/Z selectivity from methyl 5-hexynoate and (E)-10-dodecenal, which could be prepared easily from 1-decyne and 1-pentyne, respectively, with (S)-α,α-dimethylprolinol as the chiral source.

Graphical abstract: Aerobic oxidation and EATA-based highly enantioselective synthesis of lamenallenic acid

Supplementary files

Article information

Article type
Research Article
Submitted
07 Dec 2016
Accepted
06 Feb 2017
First published
08 Feb 2017
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2017,4, 951-957

Aerobic oxidation and EATA-based highly enantioselective synthesis of lamenallenic acid

X. Jiang, Y. Xue and S. Ma, Org. Chem. Front., 2017, 4, 951 DOI: 10.1039/C6QO00785F

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