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一种新型手性亚砜酰胺单膦配体:立体发散合成及其在手性金(I)催化环加成反应中的应用。

A new type of chiral sulfinamide monophosphine ligands: stereodivergent synthesis and application in enantioselective gold(I)-catalyzed cycloaddition reactions.

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy.

出版信息

Angew Chem Int Ed Engl. 2014 Apr 22;53(17):4350-4. doi: 10.1002/anie.201401067. Epub 2014 Mar 20.

DOI:10.1002/anie.201401067
PMID:24652597
Abstract

A simple, new type of chiral sulfinamide monophosphines, the so-called Ming-Phos ligands, is reported; these ligands could be easily prepared from inexpensive and commercially available starting materials. The Ming-Phos ligands performed well in the enantioselective gold-catalyzed cycloaddition reaction of 2-(1-alkynyl)-alk-2-en-1-ones with nitrones. Both enantiomers of the products could be obtained in good yields and with excellent diastereo- and enantioselectivity through transformations that were catalyzed by gold complexes derived from two diastereomers of Ming-Phos ligand M5 (Ar=1-naphthyl).

摘要

报告了一种简单的新型手性亚砜单膦配体,即所谓的 Ming-Phos 配体;这些配体可以很容易地由廉价且市售的起始原料制备。在金催化的 2-(1-炔基)-烷-2-烯-1-酮与亚硝酮的对映选择性环加成反应中,Ming-Phos 配体表现良好。通过金配合物催化的转化,可以以良好的产率和优异的非对映选择性和对映选择性获得产物的两种对映异构体,该金配合物衍生自 Ming-Phos 配体 M5 的两种非对映异构体(Ar=1-萘基)。

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