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Synlett 2014; 25(12): 1776-1780
DOI: 10.1055/s-0034-1378204
DOI: 10.1055/s-0034-1378204
letter
Switching Enantioface Selection in the Asymmetric Nitro-Mannich Reaction Using Single Chiral Bis(imidazolidine)pyridine–Metal Catalysts
Further Information
Publication History
Received: 07 April 2014
Accepted after revision: 01 May 2014
Publication Date:
03 June 2014 (online)
![](https://www.thieme-connect.de/media/synlett/201412/lookinside/thumbnails/10.1055-s-0034-1378204-1.jpg)
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
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
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Reviews of enantiofacial switching:
Recent examples of enantiofacial switching:
Catalytic asymmetric nitro-Mannich reaction using Cu complex:
Catalytic asymmetric nitro-Mannich reaction using Zn complex:
Catalytic asymmetric nitro-Mannich reaction using heterobimetallic system:
Representative examples of catalytic asymmetric nitro-Mannich reaction using organocatalyst: