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Most Requested Journal Articles 2Q02-Chemistry and Related

Following is one of the documents most requested by researchers using CAS electronic products.

CAS indexed 44 chemical substances from this document.
CAS subject entries for this document include: Green chemistry; Molecular mechanics; Diels-Alder reaction; and 2 additional concepts.

TITLE:	The First General Enantioselective Catalytic Diels-Alder Reaction with Simple .alpha.,.beta.-Unsaturated Ketones
AUTHOR(S):	Northrup, Alan B.; MacMillan, David W. C.
CORPORATE SOURCE:	Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, 91125, USA
SOURCE:	Journal of the American Chemical Society (2002), 124(11), 2458-2460 CODEN: JACSAT; ISSN: 0002-7863
PUBLISHER:	American Chemical Society
LANGUAGE:	English

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] cycloaddns. 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 obsd. for all reactions conducted during the course of this study.

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Updated 5/7/2007 11:05:17 AM