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Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes

Khrakovsky, Dimitri A. and Tao, Chuanzhou and Johnson, Miles W. and Thornbury, Richard T. and Shevick, Sophia L. and Toste, F. Dean (2016) Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes. Angewandte Chemie International Edition, 55 (20). pp. 6079-6083. ISSN 1433-7851. https://resolver.caltech.edu/CaltechAUTHORS:20160425-131647236

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Abstract

The gold-catalyzed enantioselective hydroazidation and hydroamination reactions of allenes are presented herein. ADC gold(I) catalysts derived from BINAM were critical for achieving high levels of enantioselectivity in both transformations. The sense of enantioinduction is reversed for the two different nucleophiles, allowing access to both enantiomers of the corresponding allylic amines using the same catalyst enantiomer.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201601550DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201601550/abstractPublisherArticle
ORCID:
AuthorORCID
Toste, F. Dean0000-0001-8018-2198
Additional Information:© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: February 12, 2016; First published: 20 April 2016. We gratefully acknowledge NIHGMS (RO1 GM073932) for financial support. D.A.K. gratefully acknowledges the Novartis Graduate Fellowship. C.T. thanks Huaihai Institute of Technology and the Jiangsu Provincial Department of Education for financial support. M.W.J. gratefully acknowledges the NSF (GRFP No. DGE1106400) and UC Berkeley for a Chancellor's Fellowship. We thank William J. Wolf and College of Chemistry CheXray (NIH Shared Instrumentation Grant S10-RR027172) for X-ray crystallographic data. We also thank Robert Bergman, David Nagib, Hosea Nelson, Matthew Winston, and Weiwei Zi for helpful discussions.
Funders:
Funding AgencyGrant Number
NIHRO1 GM073932
NovartisUNSPECIFIED
Huaihai Institute of TechnologyUNSPECIFIED
Jiangsu Provincial Department of EducationUNSPECIFIED
NSF Graduate Research FellowshipDGE-1106400
University of California, BerkeleyUNSPECIFIED
NIHS10-RR027172
Subject Keywords:acyclic diaminocarbene; enantioselective synthesis; gold catalysis; hydroamination; hydroazidation
Issue or Number:20
Record Number:CaltechAUTHORS:20160425-131647236
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160425-131647236
Official Citation:D. A. Khrakovsky, C. Tao, M. W. Johnson, R. T. Thornbury, S. L. Shevick, F. D. Toste, Angew. Chem. Int. Ed. 2016, 55, 6079
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66454
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:03 May 2016 03:01
Last Modified:28 Oct 2019 18:16

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