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钯催化的亚砜阴离子对映选择性烯丙基化反应。

Palladium-Catalyzed Enantioselective Alkenylation of Sulfenate Anions.

机构信息

Roy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.

Natural Medicine Research Center, College of Veterinary Medicine , Sichuan Agricultural University , Chengdu 611130 , People's Republic of China.

出版信息

Org Lett. 2019 Feb 15;21(4):960-964. doi: 10.1021/acs.orglett.8b03943. Epub 2019 Jan 29.

Abstract

A novel approach to synthesize enantio-enriched alkenyl/aryl sulfoxides is achieved by using CsF to generate sulfenate anions and conducting the catalytic enantioselective alkenylation with [Pd(allyl)Cl]/(2 R)-1-[(1 R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene (SL-J002-1). A wide variety of sulfoxides bearing sensitive functional groups are produced with high yields (up to 94%) and enantioselectivities (up to 92%).

摘要

通过使用 CsF 生成亚磺酸盐阴离子,并使用 [Pd(allyl)Cl]/(2R)-1-[(1R)-1-[双(1,1-二甲基乙基)膦基]乙基]-2-(二苯基膦基)二茂铁 (SL-J002-1) 进行催化对映选择性烯丙基化反应,实现了一种合成对映体富集的烯基/芳基亚砜的新方法。各种带有敏感官能团的亚砜都可以高产率(高达 94%)和对映选择性(高达 92%)得到。

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