Synfacts 2014; 10(1): 0053
DOI: 10.1055/s-0033-1340434
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Spiro-[Butyrolactone-Pyrrolidine]

Contributor(s):
Hisashi Yamamoto
,
Biplab Maji
Li Q.-H, Liu T.-L, Wei L, Zhou X, Tao H.-Y, Wang C.-J * Wuhan University and Shanghai Institute of Organic Chemistry, P. R. of China
exo-Selective Construction of Spiro-[Butyrolactone-Pyrrolidine] via 1,3-Dipolar Cycloaddition of Azomethine Ylides with α-Methylene-γ-butyrolactone Catalyzed by Cu(I)/DTBM-BIPHEP.

Chem. Commun. 2013;
49: 9642-9644
Further Information

Publication History

Publication Date:
13 December 2013 (online)

 

Significance

The authors developed an asymmetric synthesis of spiro-[butyrolactone-pyrrolidine] catalyzed by Cu(I)-DTBM-BIPHEP delivering exo-selective 1,3-dipolar cycloadducts of azo­methine ylides and α-methylene-γ-butyrolactone. In all cases excellent chemical yields and stereo­selectivities were achieved.


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Comment

Several natural alkaloids and important biological compounds contain spiro-[butyrolactone-pyrrolidine] as core structure making them very attractive targets in the synthetic community. Thus, this finding for the syntheses of bicyclic and tricyclic skeletons with multiple quaternary stereogenic centers is very attractive.


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