Enantioselective Alkenylation of Aldimines Catalyzed by a Rhodium–Diene Complex

An efficient rhodium-catalyzed asymmetric addition reaction of potassium alkenyltrifluoroborates to N-nosylaldimines has been developed. Under optimal conditions, the reactions proceeded with good to excellent yields and excellent enantioselectivities (97 → 99% ee). The utility of this method is dem...

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Bibliographic Details
Published in:Organic letters 2014-02, Vol.16 (3), p.1016-1019
Main Authors: Cui, Zhe, Chen, Ya-Jing, Gao, Wen-Yun, Feng, Chen-Guo, Lin, Guo-Qiang
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Catalysis
Ergot Alkaloids - chemical synthesis
Ergot Alkaloids - chemistry
Imines - chemistry
Molecular Structure
Rhodium - chemistry
Stereoisomerism
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Summary:An efficient rhodium-catalyzed asymmetric addition reaction of potassium alkenyltrifluoroborates to N-nosylaldimines has been developed. Under optimal conditions, the reactions proceeded with good to excellent yields and excellent enantioselectivities (97 → 99% ee). The utility of this method is demonstrated by the formal synthesis of (−)-aurantioclavine.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5000154