Synthesis 2012; 44(11): 1679-1685
DOI: 10.1055/s-0031-1290971
paper
© Georg Thieme Verlag Stuttgart · New York

Formal [4+1] Annulation of Cyclopropyl Amides and Water Mediated by Lewis Acid: A Novel Entry to γ-Butyrolactones

Dingyuan Zhang
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. of China, Fax: +86(431)85262676   eMail: ariel@ciac.jl.cn   eMail: dwdong@ciac.jl.cn
,
Rui Zhang*
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. of China, Fax: +86(431)85262676   eMail: ariel@ciac.jl.cn   eMail: dwdong@ciac.jl.cn
,
Yongjiu Liang
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. of China, Fax: +86(431)85262676   eMail: ariel@ciac.jl.cn   eMail: dwdong@ciac.jl.cn
,
Dewen Dong*
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. of China, Fax: +86(431)85262676   eMail: ariel@ciac.jl.cn   eMail: dwdong@ciac.jl.cn
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Publikationsverlauf

Received 10. Februar 2012

Accepted after revision: 28. März 2012

Publikationsdatum:
08. Mai 2012 (online)


Abstract

An efficient one-pot synthesis of substituted γ-butyrolactones from cyclopropyl amides mediated by the Lewis acid SnCl4·5H2O is reported. A mechanism involving a tandem ring-opening reaction and intramolecular cyclization reaction is proposed.

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