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Mechanistic Insights into Cu-Catalyzed Asymmetric Aldol Reactions: Chemical and Spectroscopic Evidence for a Metalloenolate Intermediate

Pagenkopf, Brian L. and Krüger, Jochen and Stojanovic, Aleksandar and Carreira, Erick M. (1998) Mechanistic Insights into Cu-Catalyzed Asymmetric Aldol Reactions: Chemical and Spectroscopic Evidence for a Metalloenolate Intermediate. Angewandte Chemie International Edition, 37 (22). pp. 3124-3126. ISSN 1433-7851. http://resolver.caltech.edu/CaltechAUTHORS:20180507-135626223

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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/(SICI)1521-3773(19981204)37:22<3124::AID-ANIE3124>3.0.CO;2-1DOIArticle
Additional Information:© 1998 Wiley‐VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany. Issue Online 17 December 1998; Version of Record online: 17 December 1998; Manuscript received: 16 June 1998. B.L.P. thanks the National Institutes of Health (NIH), J.K. thanks the Deutsche Forschungsgemeinschaft, and A.S. is grateful to the Schweizerischer Nationalfonds for postdoctoral fellowships. Financial support was provided by the Packard Foundation, National Science Foundation (USA), NIH (USA), and generous funds from Eli Lilly, Merck, Novartis, Pfizer, Upjohn, and Zeneca.
Funders:
Funding AgencyGrant Number
NIHUNSPECIFIED
Deutsche Forschungsgemeinschaft (DFG)UNSPECIFIED
Schweizerischer NationalfondsUNSPECIFIED
David and Lucile Packard FoundationUNSPECIFIED
NSFUNSPECIFIED
Eli LillyUNSPECIFIED
MerckUNSPECIFIED
NovartisUNSPECIFIED
PfizerUNSPECIFIED
UpjohnUNSPECIFIED
ZenecaUNSPECIFIED
Subject Keywords:Aldol reactions; Asymmetric catalysis; C−C coupling; IR spectroscopy
Record Number:CaltechAUTHORS:20180507-135626223
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20180507-135626223
Official Citation:Pagenkopf, B. L., Krüger, J. , Stojanovic, A. and Carreira, E. M. (1998), Mechanistic Insights into Cu‐Catalyzed Asymmetric Aldol Reactions: Chemical and Spectroscopic Evidence for a Metalloenolate Intermediate. Angewandte Chemie International Edition, 37: 3124-3126. doi:10.1002/(SICI)1521-3773(19981204)37:22<3124::AID-ANIE3124>3.0.CO;2-1
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86248
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:07 May 2018 21:19
Last Modified:07 May 2018 21:19

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