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A Substrate‐Directed Diastereoselective Synthesis of Vicinal Diamines Using an A3‐Coupling Strategy: An Application to the Total Synthesis of (+)‐ and (−)‐Epiquinamides

A Substrate‐Directed Diastereoselective Synthesis of Vicinal Diamines Using an A3‐Coupling... A copper‐catalyzed highly diastereoselective multicomponent reaction (MCR) of α‐amino aldehydes, dibenzylamine and various alkynes leading to propargyl syn 1,2‐diamines has been established. The methodology has been further supported by the total synthesis of (+)‐ and (−)‐epiquinamides from A3‐coupled adducts derived from l‐ and d‐pipecolic acids, respectively, in overall yields of 31 %. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

A Substrate‐Directed Diastereoselective Synthesis of Vicinal Diamines Using an A3‐Coupling Strategy: An Application to the Total Synthesis of (+)‐ and (−)‐Epiquinamides

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References (60)

Publisher
Wiley
Copyright
© 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201700049
Publisher site
See Article on Publisher Site

Abstract

A copper‐catalyzed highly diastereoselective multicomponent reaction (MCR) of α‐amino aldehydes, dibenzylamine and various alkynes leading to propargyl syn 1,2‐diamines has been established. The methodology has been further supported by the total synthesis of (+)‐ and (−)‐epiquinamides from A3‐coupled adducts derived from l‐ and d‐pipecolic acids, respectively, in overall yields of 31 %.

Journal

Asian Journal of Organic ChemistryWiley

Published: May 1, 2017

Keywords: ; ; ; ;

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