Synlett 2016; 27(11): 1699-1702
DOI: 10.1055/s-0035-1561956
letter
© Georg Thieme Verlag Stuttgart · New York

A Formal Enantioselective Synthesis of (–)-Epiquinamide by Proline-Catalyzed One-Pot Sequential α-Amination/Propargylation of Aldehyde and Asymmetric Dihydroxylation of Olefin

Brij Bhushan Ahuja
a   National Chemical Laboratory, Chemical Engineering & Process Development Division, Pune 411008, Maharastra, India   Email: a.sudalai@ncl.res.in
,
Lourdusamy Emmanuvel
b   Karunya University, Department of Chemistry, Coimbatore 641114, Tamil Nadu, India   Email: emmanuvel@karunya.edu
,
Arumugam Sudalai*
a   National Chemical Laboratory, Chemical Engineering & Process Development Division, Pune 411008, Maharastra, India   Email: a.sudalai@ncl.res.in
› Author Affiliations
Further Information

Publication History

Received: 09 November 2015

Accepted after revision: 04 March 2016

Publication Date:
07 April 2016 (online)


Abstract

Two independent routes to the formal synthesis of (–)-epiquinamide, have been described: the first route utilizes an l -proline-catalyzed one-pot sequential α-amination/propargylation of aldehyde, while the second one employs asymmetric dihydroxylation as the key reaction to install the stereochemistry. While the first synthesis was accomplished in nine steps with 24.4% overall yield and dr 9:1, the second strategy resulted in the synthesis in eight steps with 36.4% overall yield and with perfect enantiocontrol.

Supporting Information