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Synfacts 2014; 10(1): 0053
DOI: 10.1055/s-0033-1340434
DOI: 10.1055/s-0033-1340434
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Synthesis of Spiro-[Butyrolactone-Pyrrolidine]
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
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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