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Synfacts 2013; 9(7): 0737
DOI: 10.1055/s-0033-1339171
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cr/Salen-Catalyzed Nazarov Cyclization of Dienones

Contributor(s):
Hisashi Yamamoto
,
Jiajing Tan
Hutson GE, Türkmen YE, Rawal VH * The University of Chicago, USA
Salen Promoted Enantioselective Nazarov Cyclizations of Activated and Unactivated Dienones.

J. Am. Chem. Soc. 2013;
135: 4988-4991
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Further Information

Publication History

Publication Date:
17 June 2013 (online)

 
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Key words

chromium - salen - Nazarov cyclization - dienones

Significance

Rawal and co-workers describe the highly enantioselective Cr/salen-catalyzed ­Nazarov cyclization of both activated and unactivated dienones, giving the desired hydrindenone products with three contiguous chiral centers in moderate to good yields and stereoselectivities.


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Comment

This paper represents the first example of highly enantioselective Nazarov reactions of unactivated dienones. A one-point activation mode was proposed and a counter-clockwise conrotatory cyclization would release the R group into a less sterically congested environment.


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