cis-2,3-Disubstituted Cyclopropane 1,1-Diesters in [3 + 2] Annulations with Aldehydes: Highly Diastereoselective Construction of Densely Substituted Tetrahydrofurans

Autor:	Yongxian Sun, Shuang-Liu Zhou, Yue Shen, Jiang Chu, Gaosheng Yang, Jun Chai, Zhuo Chai
Rok vydání:	2013
Předmět:	Cyclopropanes Aldehydes Annulation Molecular Structure Chemistry Organic Chemistry Diastereomer Esters Stereoisomerism Cyclopropane chemistry.chemical_compound Organic chemistry Molecule Stereoselectivity Furans
Zdroj:	The Journal of Organic Chemistry. 78:5393-5400
ISSN:	1520-6904 0022-3263
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5625b4ad458f8f9a6c12175a6874d602 https://doi.org/10.1021/jo400554a Zobrazit plný text záznamu