Asymmetric Synthesis of 2‐Heteroaryl Cyclic Amines: Total Synthesis of (–)‐Anabasine. Issue 20 (3rd June 2014)

• Record Type: Journal Article
• Authors: Sallio, Romain; Lebrun, Stéphane; Gigant, Nicolas; Gillaizeau, Isabelle; Deniau, Eric
• Is Part Of: European journal of organic chemistry. Issue 20(2014)
• Page Start: 4381
• Page End: 4388
• Publication Date: 2014-06-03
• Subjects: Synthetic methods -- Asymmetric synthesis -- Chiral auxiliaries -- Cross‐cou­pling -- Amines; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402202
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A new and concise method for the synthesis of enantioenriched 2‐heteroaryl cyclic amines was developed through an intramolecular chirality transfer. The influence of the nature of both ring size and heteroaryl moiety was investigated. The versatility of this reaction was demonstrated by the enantioselective synthesis of (–)‐anabasine. Abstract : An asymmetric synthesis of a variety of 2‐heteroaryl cyclic amines through a ( S )‐aminomethylprolinol chiral pool strategy is described. This route was applied for the total synthesis of (–)‐anabasine.