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Multicatalytic Enantioselective Borrowing Hydrogen δ-Lactonization Strategy from β-Keto Esters and Allylic Alcohols
Synthesis ( IF 2.6 ) Pub Date : 2017-09-07 , DOI: 10.1055/s-0036-1588547
Adrien Quintard , Mylène Roudier , Jean Rodriguez

Published as part of the Bürgenstock Special Section 2017 Future Stars in Organic Chemistry

Abstract

By combining an iron-catalyzed borrowing hydrogen of allylic alcohols with an enantioselective organocatalyzed Michael addition of β-keto esters followed by a subsequent DBU-promoted lactonization different enantioenriched δ-lactones have been synthesized with good enantioselectivities. The valuable building blocks, featuring in some cases challenging quaternary stereocenters, have been obtained with >90% ee.

By combining an iron-catalyzed borrowing hydrogen of allylic alcohols with an enantioselective organocatalyzed Michael addition of β-keto esters followed by a subsequent DBU-promoted lactonization different enantioenriched δ-lactones have been synthesized with good enantioselectivities. The valuable building blocks, featuring in some cases challenging quaternary stereocenters, have been obtained with >90% ee.



中文翻译:

β-酮酯和烯丙醇的多催化对映选择氢δ-内酯化策略

作为Bürgenstock专栏2017年有机化学中的未来之星的一部分发布

抽象的

通过将铁催化的烯丙醇的借入氢与β-酮酯的对映选择性有机催化的迈克尔加成反应相结合,随后进行DBU促进的内酯化,合成了具有良好对映选择性的各种对映体富集的δ-内酯。ee大于90%时,已经获得了有价值的构件,在某些情况下具有挑战性的四元立体中心。

通过将铁催化的烯丙醇的借入氢与β-酮酯的对映选择性有机催化的迈克尔加成反应相结合,随后进行DBU促进的内酯化,合成了具有良好对映选择性的各种对映体富集的δ-内酯。ee大于90%时,已经获得了有价值的构件,在某些情况下具有挑战性的四元立体中心。

更新日期:2017-09-07
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