601-53-6Relevant articles and documents
Reduction of a Δ4-steroid with diborane
D'Alessandro,Giacopello,Seldes,Deluca
, p. 2703 - 2708 (1995)
Reported here is a boron process equivalent to stereoselective olefin reduction and concomitant protecting group cleavage.
Iron-Catalyzed Chemoselective Reduction of α,β-Unsaturated Ketones
Lator, Alexis,Gaillard, Sylvain,Poater, Albert,Renaud, Jean-Luc
supporting information, p. 5770 - 5774 (2018/03/26)
An iron-catalyzed chemo- and diastereoselective reduction of α,β-unsaturated ketones into the corresponding saturated ketones in mild reaction conditions is reported herein. DFT calculations and experimental work underline that transfer hydride reduction is a more facile process than hydrogenation, unveiling the fundamental role of the base.
Direct organocatalytic stereoselective transfer hydrogenation of conjugated olefins of steroids
Ramachary, Dhevalapally B.,Sakthidevi, Rajasekar,Reddy, P. Srinivasa
, p. 13497 - 13506 (2013/09/02)
Kinetically controlled and organocatalytic syn-selective transfer hydrogenation has been successfully demonstrated for the reduction of the enone functional group of various steroids. Herein, diastereoselective synthesis of many 5β-steroids have been reported through organocatalysis, which have broad medicinal and pharmaceutical applications. The mechanistic studies and the selectivity of the products clearly indicated that the catalyst 1b·d-CSA is mild enough to activate the various chiral cyclic enones through iminium ion formation during the organocatalytic transfer hydrogenations with Hantzsch ester 2a as a hydrogen source. Further, clear evidence for the selective formation of intermediate iminium species [I]+ have been characterized through on-line monitoring of controlled experiments by NMR and ESI-HRMS analyses.
