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Synfacts 2015; 11(1): 0055
DOI: 10.1055/s-0034-1379752
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Asymmetric Claisen Rearrangement

Contributor(s):
Hisashi Yamamoto
,
Ramesh C. Samanta
Liu Y, Hu H, Zheng H, Xia Y, Liu X, Lin L, Feng X * Sichuan University, Chengdu and Lanzhou University, P. R. of China
Nickel(II)-Catalyzed Asymmetric Propargyl and Allyl Claisen Rearrangements to Allenyl- and Allyl-Substituted β-Ketoesters.

Angew. Chem. Int. Ed. 2014;
53: 11579-11582
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

Claisen rearrangement - allenyls - nickel

Significance

The authors present an asymmetric propargyl and allyl Claisen rearrangement using a readily available chiral N,N′-dioxide–nickel(II) complex. Product allyl and allenyl compounds were obtained with good yield and excellent enantio- and diastereoselectivities.


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Comment

This rearrangement works with relatively inexpensive metal (nickel) under mild reaction conditions. The produced β-keto esters with all-carbon quaternary stereogenic centers with allenyl and allyl substituents are highly useful chiral building blocks.


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