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Mechanistic Insights into Cu‐Catalyzed Asymmetric Aldol Reactions: Chemical and Spectroscopic Evidence for a Metalloenolate Intermediate
Author(s) -
Pagenkopf Brian L.,
Krüger Jochen,
Stojanovic Aleksandar,
Carreira Erick M.
Publication year - 1998
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/(sici)1521-3773(19981204)37:22<3124::aid-anie3124>3.0.co;2-1
Subject(s) - transmetalation , aldol reaction , catalysis , catalytic cycle , chemistry , photochemistry , reactive intermediate , spectroscopy , reaction intermediate , organic chemistry , physics , quantum mechanics
In situ IR spectroscopy and transmetalation experiments confirm a postulated catalytic cycle. The metalloenolate 1 describes the active intermediate in the aldol reaction catalyzed by [CuF 2 {( S )‐tol‐binap}] (see reaction scheme). ( S )‐tol‐binap=( S )‐(−)‐2,2′‐bis(di‐ p ‐tolylphosphanyl)‐1,1′‐binaphthyl.