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外消旋和非对映选择性合成过氧缩醛:有机催化的过氧半缩醛化/氧杂-Michael 加成级联反应。

Enantio- and Diastereoselective Synthesis of exo-Peroxyacetals: An Organocatalyzed Peroxyhemiacetalization/oxa-Michael Addition Cascade.

机构信息

Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal-, 462066, India.

出版信息

Angew Chem Int Ed Engl. 2016 Jun 27;55(27):7723-7. doi: 10.1002/anie.201511165. Epub 2016 Feb 19.

Abstract

An unprecedented enantioselective peroxyhemiacetalization/oxa-Michael addition cascade of ortho-formyl homochalcones has been developed using cinchona-alkaloid-based chiral bifunctional organocatalysts to provide cis-configured exo-peroxyacetals, a new class of organic peroxide, in good yields with excellent enantio- and diastereoselectivities. The resulting cis-configured exo-peroxyacetals were converted into the corresponding trans-configured peroxyacetals without affecting the enantioselectivity. Furthermore, the displacement of the peroxide moiety of exo-peroxyacetals with various nucleophiles has been demonstrated to afford 1,3-disubstituted isochromans with high diastereoselectivities and excellent enantioselectivities.

摘要

已开发出一种前所未有的对甲酰基查耳酮的对映选择性过氧半缩醛化/氧杂-Michael 加成级联反应,使用金鸡纳生物碱衍生的手性双功能有机催化剂,以高收率和优异的对映选择性和非对映选择性提供顺式构型的外过氧乙酰酯,这是一类新型的有机过氧化物。所得的顺式构型的外过氧乙酰酯在不影响对映选择性的情况下转化为相应的反式构型的过氧乙酰酯。此外,已证明外过氧乙酰酯的过氧基部分可以被各种亲核试剂取代,从而以高非对映选择性和优异的对映选择性得到 1,3-二取代异色满。

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