Published May 10, 2016
| Accepted Version + Supplemental Material
Journal Article
Open
Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes
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.
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.Attached Files
Accepted Version - nihms800383.pdf
Supplemental Material - anie201601550-sup-0001-misc_information.pdf
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anie201601550-sup-0001-misc_information.pdf
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Additional details
- PMCID
- PMC4948301
- Eprint ID
- 66454
- Resolver ID
- CaltechAUTHORS:20160425-131647236
- RO1 GM073932
- NIH
- Novartis
- Huaihai Institute of Technology
- Jiangsu Provincial Department of Education
- DGE-1106400
- NSF Graduate Research Fellowship
- University of California, Berkeley
- S10-RR027172
- NIH
- Created
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2016-05-03Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field