Synlett 2014; 25(12): 1776-1780
DOI: 10.1055/s-0034-1378204
letter
© Georg Thieme Verlag Stuttgart · New York

Switching Enantioface Selection in the Asymmetric Nitro-Mannich Reaction Using Single Chiral Bis(imidazolidine)pyridine–Metal Catalysts

Takayoshi Arai*, Eri Matsumura
  • Department of Chemistry, Graduate School of Science, Chiba University, Inage 263-8522, Japan   Fax: +81(43)2902889   Email: tarai@faculty.chiba-u.jp
Further Information

Publication History

Received: 07 April 2014

Accepted after revision: 01 May 2014

Publication Date:
03 June 2014 (eFirst)

Abstract

Switching enantioface selection of imines in the metal-catalyzed nitro-Mannich reaction was accomplished with the same enantiomer of diamine-derived bis(imidazolidine)pyridine (PyBidine) ligand. The (S,S)-PyBidine–CoCl2 complex catalyzed the nitro-Mannich reaction of N-Ts imines to give S-enriched adducts, while the Ni(OAc)2 complex using the same ligand catalyzed the nitro-Mannich reaction of N-Boc imines in an R-stereoselective manner.

Supporting Information