Northrup, Alan B. and MacMillan, David W. C. (2002) The First General Enantioselective Catalytic Diels−Alder Reaction with Simple α,β-Unsaturated Ketones. Journal of the American Chemical Society, 124 (11). pp. 2458-2460. ISSN 0002-7863. doi:10.1021/ja017641u. https://resolver.caltech.edu/CaltechAUTHORS:20170411-135947566
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Abstract
The first general approach to enantioselective catalysis of the Diels−Alder reaction with simple ketone dienophiles has been accomplished. The use of iminium catalysis has enabled enantioselective access to a fundamental Diels−Alder reaction variant that has previously been unavailable using chiral Lewis acid catalysis. A new chiral amine catalyst has been developed that allows a variety of monodentate cyclic and acyclic ketones to successfully participate in enantioselective [4 + 2] cycloadditions. A wide spectrum of cyclic and acyclic diene substrates can also be accommodated in this new organocatalytic transformation. A computational model is provided that is in accord with the sense of enantioinduction observed for all reactions conducted during the course of this study.
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| Additional Information: | © 2002 American Chemical Society. Received 29 November 2001. Published online 23 February 2002. Published in print 1 March 2002. Financial support was provided by kind gifts from AstraZeneca, Boehringer-Ingelheim, Dupont, GlaxoSmithKline, Johnson and Johnson, Lilly, Materia, Merck Research Laboratories, Pfizer, Pharmacia, and Roche Biosciences. We also thank Great Lakes for their generous donation of (S)-phenylalanine. D.W.C.M is grateful for support from Research Corporation under the Cottrell Scholarship program. A.B.N. is grateful for a NSF predoctoral fellowship. Note Added in Proof. Shortly prior to publication it came to the authors attention that an enantioselective boron-catalyzed ketone Diels−Alder reaction has been accomplished. This work will be submitted for communication in the near future. Joel M. Hawkins, Pfizer Global Research, personal communication. | ||||||||||||||||||||||||||
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| Issue or Number: | 11 | ||||||||||||||||||||||||||
| DOI: | 10.1021/ja017641u | ||||||||||||||||||||||||||
| Record Number: | CaltechAUTHORS:20170411-135947566 | ||||||||||||||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170411-135947566 | ||||||||||||||||||||||||||
| Official Citation: | The First General Enantioselective Catalytic Diels−Alder Reaction with Simple α,β-Unsaturated Ketones Alan B. Northrup and David W. C. MacMillan Journal of the American Chemical Society 2002 124 (11), 2458-2460 DOI: 10.1021/ja017641u | ||||||||||||||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||||||||||||||
| ID Code: | 76519 | ||||||||||||||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||||||||||||||
| Deposited By: | Ruth Sustaita | ||||||||||||||||||||||||||
| Deposited On: | 11 Apr 2017 21:41 | ||||||||||||||||||||||||||
| Last Modified: | 15 Nov 2021 17:00 |
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