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cis-2,3-Disubstituted Cyclopropane 1,1-Diesters in [3 + 2] Annulations with Aldehydes: Highly Diastereoselective Construction of Densely Substituted Tetrahydrofurans
journal contribution
posted on 2013-06-07, 00:00 authored by Gaosheng Yang, Yongxian Sun, Yue Shen, Zhuo Chai, Shuangliu Zhou, Jiang Chu, Jun ChaiA 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.
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cireactivitieDensely Substituted TetrahydrofuransA seriesAnnulationCyclopropaneAldehydediastereomeric puritychemical yieldsannulation productssyntheticallypentasubstituted tetrahydrofuransaldehydemethodDiestertermDiastereoselective Constructioncyclopropanediestertrans counterpartsAlClstereoselective way
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