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Titanium‐Promoted Stereoselective Synthesis of Hydroindolones from p ‐Quinamines by Domino Conjugate Additions
Author(s) -
Carreño M. Carmen,
Ribagorda María,
Posner Gary H.
Publication year - 2002
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 - 10.1002/1521-3773(20020802)41:15<2753::aid-anie2753>3.0.co;2-m
Subject(s) - stereocenter , domino , stereoselectivity , conjugate , chemistry , titanium , stereochemistry , combinatorial chemistry , catalysis , medicinal chemistry , organic chemistry , enantioselective synthesis , mathematics , mathematical analysis
New stereogenic centers are generated in the [TiCl 2 (O i Pr) 2 ]‐catalyzed reaction of [(S) R ]‐[( p ‐tolylsulfinyl)methyl]‐ p ‐quinamines 1 with α , β ‐unsaturated ketones 2 to give hydroindole‐substituted systems 3 in a domino process. Up to four stereogenic centers are formed in the reaction of cycloalkenones and up to five when acyclic enones (2 equiv) are used.