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Synthesis of Functionalized Azetidines through Chemoselective Zinc‐Catalyzed Reduction of β‐Lactams with Silanes
Author(s) -
Alcaide Benito,
Almendros Pedro,
Aragoncillo Cristina,
GómezCampillos Gonzalo
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300320
Subject(s) - chemistry , enantiopure drug , silanes , zinc , catalysis , cyanohydrin , allene , catalytic cycle , combinatorial chemistry , organic chemistry , enantioselective synthesis , silane
An efficient method for the one‐step conversion of β‐lactams to their corresponding functionalized azetidines has been developed. This approach takes advantage of the selective reduction of the 2‐azetidinone nucleus with hydrosilanes in the presence of a zinc‐based catalyst. The methodology is tolerant towards sensitive groups such as allene, ester, and cyanohydrin moieties. In addition, the process allows the preparation of enantiopure azetidines without erosion of the stereochemical integrity. A catalytic cycle involving an azetidinium salt intermediate has been proposed.