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Stereospecific Reactions Leading to Allylboronic Esters Within Acyclic Systems Bearing Distant Stereocenters
Author(s) -
Pierrot David,
Marek Ilan
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202010135
Subject(s) - stereocenter , exergonic reaction , regioselectivity , chemistry , stereospecificity , combinatorial chemistry , stereochemistry , molecule , methanol , catalysis , enantioselective synthesis , organic chemistry
The preparation of acyclic molecules featuring congested stereocenters in a 1,4‐relationship in only three catalytic steps from commercially available building blocks is reported. This approach involves a diastereoselective diboration of alkenyl cyclopropyl methanol derivatives followed by a regioselective exergonic ring fragmentation. The starting materials can be prepared enantiomerically enriched and all substituents can be interconverted, therefore, this strategy allows a large variety of diversely functionalized allylboronic esters possessing distant tetrasubstituted stereocenters with high diastereoselectivity.