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Synthesis 2016; 48(22): 3890-3906
DOI: 10.1055/s-0035-1562793
DOI: 10.1055/s-0035-1562793
short review
The Diamino Analogues of Privileged Corey–Bakshi–Shibata and Jørgensen–Hayashi Catalysts: A Comparison of Their Performance
Further Information
Publication History
Received: 28 June 2016
Accepted: 29 June 2016
Publication Date:
01 September 2016 (online)
Abstract
α,α-Diarylprolinol derivatives are well-established families of organocatalysts that are widely used to promote diverse asymmetric reactions. The enantioinduction generated from these ligands is mainly due to the gem-diphenyl carbinol fragment. For this reason, the synthesis of diaza analogues seemed an evident and attractive issue to address in the development of alternative chiral ligands. Although the O→N substitution and subsequent derivatization at first glance looked simple, it was necessary to deal with various unexpected synthetic difficulties. It was established that suitable modifications of the side chain in the diaza analogues afford reaction yields and stereoselectivities that are comparable to those exhibited by the amino alcohol analogues. Nevertheless, various potential applications still remain undeveloped.
1 Introduction
2 Oxazaborolidines and Diazaborolidines in Borane-Mediated Reduction of Prochiral Ketones
3 Organocatalyzed Asymmetric Epoxidations
4 Assessing the Organocatalytic Capability of the α,α-Diphenylprolinol Diaza-Analogues through Benchmark Mannich and Michael Reactions
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For more recent reports, see:
For excellent reviews regarding enantioselective reduction of ketones with chiral oxazaborolidines employed as catalysts, and mechanistic considerations, see:
Also in 2008, Ooi and co-workers described the preparation of several chiral diamines derived from l-valine, l-isoleucine, and l-tert-leucine via azidation of the corresponding diarylamino alcohols:
Furthermore, some years later Lee and co-workers prepared a series of chiral amino azides, employing a biphasic reaction media of H2SO4/toluene:
Other groups have also evaluated (S)-2-(azidodiphenylmethyl)pyrrolidine and derivatives:
Varied reports from diverse research groups:
Interesting and innovative applications are compiled in the following reviews:
Other pyrrolidine derivatives with bulky substituents in the 2-position also directs the enamine attack from the opposite face such as 2-tritylpyrrolidine described in: