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J Org Chem. 2013 Jun 7;78(11):5393-400. doi: 10.1021/jo400554a. Epub 2013 May 9.

cis-2,3-Disubstituted cyclopropane 1,1-diesters in [3 + 2] annulations with aldehydes: highly diastereoselective construction of densely substituted tetrahydrofurans.

Author information

  • 1Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China. gshyang@mail.ahnu.edu.cn

Abstract

A series of cis-2,3-disubstituted cyclopropane 1,1-diesters were examined in the AlCl3-promoted [3 + 2]-annulations with aldehydes. In this reaction, these cis-cyclopropanes displayed reactivities starkly different from their trans counterparts in terms of the high chemical yields (up to 98%) and provided the desired annulation products with excellent diastereomeric purity. This protocol provides a facile and highly stereoselective way to construct synthetically useful pentasubstituted tetrahydrofurans not easily accessible using other methods.

PMID:
23634966
[PubMed - indexed for MEDLINE]
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