Premium
Catalytic Enantioselective Carboannulation with Allylsilanes
Author(s) -
BallJones Nicolas R.,
Badillo Joseph J.,
Tran Ngon T.,
Franz Annaliese K.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201403607
Subject(s) - enantioselective synthesis , chemistry , oxindole , catalysis , stereoselectivity , annulation , trifluoromethyl , malonate , carbocation , organocatalysis , stereocenter , stereochemistry , organic chemistry , medicinal chemistry , alkyl
Abstract The first catalytic asymmetric carboannulation with allylsilanes is presented. The enantioselective [3+2] annulation is catalyzed using a scandium(III)/indapybox complex with tetrakis‐[3,5‐bis(trifluoromethyl)phenyl]‐borate (BArF) to enhance catalytic activity and control stereoselectivity. Functionalized cyclopentanes containing a quaternary carbon center are derived from alkylidene oxindole, coumarin, and malonate substrates with high stereoselectivity. The enantioselective 1,4‐conjugate addition and enantioselective lactone formation (by trapping of the β‐silyl carbocation) is also described.