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Synthesis of Air‐ and Moisture‐Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction
Author(s) -
Das Braja Gopal,
Nallagonda Rajender,
Dey Dhananjay,
Ghorai Prasanta
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501914
Subject(s) - enantiopure drug , enantioselective synthesis , imine , catalysis , chemistry , moisture , hydride , substrate (aquarium) , combinatorial chemistry , organic chemistry , hydrogen , oceanography , geology
Air‐/moisture‐stable, crystalline, and storable chiral salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α‐amino esters, γ‐ and δ‐lactams, and isoindolinones have also been carried out using this methodology. Finally, the method has been applied to synthetic targets of pharmaceutical relevance, such as R ‐(+)‐salsolidine and R ‐(+)‐crispine A.