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 |
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Rok vydání: | 2013 |
Předmět: | |
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 |
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