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[3+2] and [4+1] Cycloaddition Reactions of Fischer Alkoxy(alkenyl)carbene Complexes with Electronically Neutral 1,3‐Dienes
Author(s) -
Barluenga José,
López Salomé,
Flórez Josefa
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200390087
Subject(s) - carbene , cycloaddition , alkoxy group , chemistry , enantiomer , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl
Regio‐ and stereochemically controlled formation of cyclopentenes has been achieved through the reaction of transition‐metal–alkoxy(alkenyl)carbene complexes and neutral 1,3‐dienes (see scheme; BHT=2,6‐di‐ tert ‐butyl‐4‐methylphenol). Reaction conditions dictate whether [3+2] or [4+1] cycloaddition products are obtained; alkenyl‐substituted cyclopentanones of high enantiomeric purity are synthesized by using 8‐phenylmenthyloxycarbene complexes.