Silver(I)-mediated highly enantioselective synthesis of axially chiral allenes under thermal and microwave-assisted conditions

Vanessa Kar-Yan Lo; Cong-Ying Zhou; Man-Kin Wong; Chi-Ming Che

doi:10.1039/b914516h

Silver(I)-mediated highly enantioselective synthesis of axially chiral allenes under thermal and microwave-assisted conditions

Chem Commun (Camb). 2010 Jan 14;46(2):213-5. doi: 10.1039/b914516h. Epub 2009 Sep 16.

Authors

Vanessa Kar-Yan Lo¹, Cong-Ying Zhou, Man-Kin Wong, Chi-Ming Che

Affiliation

¹ Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, China.

PMID: 20024329
DOI: 10.1039/b914516h

Abstract

Silver(I) salts mediated stereospecific transformation of optically active propargylamines to axially chiral allenes with excellent enantioselectivities (17 examples with 96-99% ee; one substrate with 91% ee) without subsequent racemization.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkadienes / chemical synthesis*
Alkadienes / chemistry
Catalysis
Microwaves*
Pargyline / analogs & derivatives
Pargyline / chemistry
Propylamines / chemistry
Silver / chemistry*
Stereoisomerism
Temperature

Substances

Alkadienes
Propylamines
propargylamine
Silver
propadiene
Pargyline