钯/布朗斯特酸催化的手性亚磺酰胺作为亲核试剂的非对映选择性环化反应。
Palladium/Brønsted-Acid-Catalyzed Diastereoselective Cyclization with Chiral Sulfinamides as Nucleophiles.
机构信息
Department of Chemistry, Tunghai University, Taichung City 40704, Taiwan.
出版信息
J Org Chem. 2021 Sep 3;86(17):12354-12366. doi: 10.1021/acs.joc.1c01301. Epub 2021 Aug 17.
PMID:34402303
Abstract
This article reports diastereoselective cyclization with chiral sulfinamides as nucleophiles in two reaction pathways: (1) intramolecular allylic substitution and (2) sequential aerobic oxidation with aza-Michael addition. These reactions were enabled by synergistic palladium and Brønsted acid catalysis and produced chiral isoindolines with good yields of 55-92% and high diastereoselectivities of 10:1 to >20:1 dr.
摘要
本文报道了手性亚磺酰胺作为亲核试剂在两条反应途径中进行非对映选择性环化反应
（1）分子内烯丙基取代和（2）顺序有氧氧化与氮杂迈克尔加成。这些反应通过协同钯和布朗斯台德酸催化实现，得到了具有良好产率（55-92%）和高非对映选择性（10:1 至>20:1 dr）的手性异吲哚啉。
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