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Enantioselective γ-lactam synthesis via palladium-catalyzed intramolecular asymmetric allylic alkylation

Bantreil, Xavier and Prestat, Guillaume and Madec, David and Fristrup, Peter and Poli, Giovanni (2009) Enantioselective γ-lactam synthesis via palladium-catalyzed intramolecular asymmetric allylic alkylation. Synlett, 2009 (9). pp. 1441-1444. ISSN 0936-5214 http://resolver.caltech.edu/CaltechAUTHORS:20090729-121619864

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Abstract

A Pd(0)-catalyzed intramolecular allylic alkylation in the presence of (R)-3,5-t-Bu-MeOBIPHEP takes place in up to 92:8 er in agreement with DFT calculations and provides easy access to enantioenriched disubstituted γ-lactams.


Item Type:Article
Additional Information:© 2009 Georg Thieme Verlag. Received: 13 February 2009; publication Date: 04 May 2009 (eFirst); 03 June 2009 (Print). CNRS and UPMC are acknowledged for financial support. The sponsorship of COST Action D40 ‘Innovative Catalysis: New Processes and Selectivities' is kindly acknowledged. PF thanks the Carlsberg and Lundbeck foundations for financial support. We thank Solvias for a gift of ligands, Prof. P. S. Pregosin for a sample of ligand L5, Prof. J.-P. Genêt for a sample of ligand L3, and Prof. P.-O. Norrby for fruitful discussions.
Funders:
Funding AgencyGrant Number
Conseil National de la Recherche Scientifique, CNRSUNSPECIFIED
Université Pierre et Marie CurieUNSPECIFIED
Carlsberg FoundationUNSPECIFIED
Lundbeck FoundationUNSPECIFIED
Subject Keywords:palladium; allylic alkylation; enantioselectivity
Record Number:CaltechAUTHORS:20090729-121619864
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20090729-121619864
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:14724
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:07 Aug 2009 19:55
Last Modified:26 Dec 2012 11:07

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