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。