Premium
Regiodivergent Epoxide Opening: A Concept in Stereoselective Catalysis beyond Classical Kinetic Resolutions and Desymmetrizations
Author(s) -
Gansäuer Andreas,
Fan ChunAn,
Keller Florian,
Karbaum Peter
Publication year - 2007
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.200701021
Subject(s) - epoxide , stereoselectivity , kinetic resolution , catalysis , chemistry , enantioselective synthesis , stereochemistry , kinetic energy , organic chemistry , physics , classical mechanics
An approach to highly regiodivergent epoxide openings (REOs) is presented. The very popular kinetic resolutions of epoxides and openings of meso ‐epoxides constitute subclasses of such REOs. REOs are attractive for parallel resolutions, double asymmetric reactions of enantiomerically enriched epoxides, and for semisynthetic applications in the functionalization of natural products. They have been notoriously difficult to realize by means of S N 2 mechanisms. Our titanocene‐catalyzed radical REO addresses this issue by decoupling epoxide opening and radical trapping and is firmly based on a mechanistic study of the reductive epoxide opening.