A Rhodium(I)-Catalyzed Formal Allenic Alder Ene Reaction for the Rapid and Stereoselective Assembly of Cross-Conjugated Trienes

A rhodium(I)-catalyzed allenic Alder ene reaction to prepare cross-conjugated trienes has been discovered. The scope and limitations are currently being investigated, and the results obtained to date are reported on. This method shows enticing functional group compatibility by tolerating terminal an...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-12, Vol.124 (51), p.15186-15187
Main Authors: Brummond, Kay M, Chen, Hongfeng, Sill, Peter, You, Lingfeng
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Alkenes - chemistry
Alkynes - chemistry
Catalysis
Chemical reactivity
Chemistry
Cyclization
Exact sciences and technology
Hydrocarbons, Cyclic - chemical synthesis
Organic chemistry
Organometallic Compounds - chemistry
Reactivity and mechanisms
Rhodium - chemistry
Stereoisomerism
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Summary:A rhodium(I)-catalyzed allenic Alder ene reaction to prepare cross-conjugated trienes has been discovered. The scope and limitations are currently being investigated, and the results obtained to date are reported on. This method shows enticing functional group compatibility by tolerating terminal and internal alkynes, hydroxyl, sulfonamide, ether, and diester groups. Progress has been made to increase the stereoselectivity of the olefinic side chain via an unprecendented iridium(I) catalyzed Alder−ene reaction.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja027588p