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Sulfur‐Functionalized Olefins for Titanacycle Formation: Tandem Asymmetric Cyclization and the Pummerer Reaction Based on Sulfoxides Promoted by Titanium( II )‐to‐Titanium( IV ) Relay
Author(s) -
Narita Miho,
Urabe Hirokazu,
Sato Fumie
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(20021004)41:19<3671::aid-anie3671>3.0.co;2-x
Subject(s) - sulfoxide , titanium , tandem , chemistry , reagent , pummerer rearrangement , sulfur , combinatorial chemistry , cascade reaction , organic chemistry , polymer chemistry , catalysis , materials science , acetic anhydride , composite material
Reusing the metal : Combination of the sulfoxide‐based asymmetric enyne cyclization (Ti II mediated) and the Pummerer reaction (Ti IV mediated) in tandem was effected by a reagent system consisting of a relay of titanium( II ) to titanium( IV ), which permits a one‐pot synthesis of cyclic aldehydes in an optically active form (see scheme; Tol= p ‐tolyl).