Stereoselective oxy-homo-Michael reactions of enantioenriched bicyclic donor-acceptor cyclopropanes to afford optically active trans-α,β-disubstituted γ-butyrolactones possessing three serial chiral centers
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- 作者：Seijiro Takada ; Kiitsu Iwata ; Toshihide Yubune ; Yoshinori Nishii ; nishii@shinshu-u.ac.jp" class="auth_mail" title="E-mail the corresponding author
- 关键词：Oxy-homo-Michael reaction ; Donor&ndash ; acceptor cyclopropane ; trans-α ; β-Disubstituted γ-butyrolactone ; Cyclopropane ring opening ; Stereoselective protonation
- 刊名：Tetrahedron Letters
- 出版年：2016
- 出版时间：1 June 2016
- 年：2016
- 卷：57
- 期：22
- 页码：2422-2425
- 全文大小：995 K
文摘
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Stereoselective oxy-homo-Michael reaction with excellent dr and ee.
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Backside attack of nucleophiles and cyclopropane cleavage occurred at the same time.
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Highly stereoselective protonation of the enolate gave trans-γ-butyrolactone.
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Trimethoxyphenyl group enhanced the epimerization process of products.
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Increasing the alcohols to two equivalents improved the diastereoselectivity.