Reversal of enantioselectivity induced by the achiral part of an organocatalyst in a Diels-Alder reaction

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• 作者：Trupti S. Tawde ; Swapnil J. Wagh ; Jai V. Sapre ; Vaibhav N. Khose ; Purav M. Badani ; Anil V. Karnik ; ^{avkarnik@chem.mu.ac.in" class="auth_mail" title="E-mail the corresponding author}
• 刊名：Tetrahedron: Asymmetry
• 出版年：2016
• 出版时间：15 February 2016
• 年：2016
• 卷：27
• 期：2-3
• 页码：130-135
• 全文大小：585 K

文摘

A new series of chiral organocatalysts was developed by attaching achiral heterocyclic units via a methylene group to (S)-2-hydroxyethylbenzimidazole for the asymmetric Diels–Alder reaction between anthrone enolate and maleimides. While organocatalysts with pyridine, quinoline, and 1,3,4-oxadiazole achiral heterocyclic subunits gave Diels–Alder adducts with an (S,S)-configuration, the organocatalyst with a benzotriazole subunit caused formation of the (R,R)-configuration for the Diels–Alder adducts