An Organocatalytic Asymmetric Friedel-Crafts Addition/Fluorination Sequence: Construction of Oxindole-Pyrazolone Conjugates Bearing Vicinal Tetrasubstituted Stereocenters

被引：116

作者：

Bao, Xiaoze ^{[1
]}

Wang, Baomin ^{[1
]}

Cui, Longchen ^{[1
]}

Zhu, Guodong ^{[1
]}

He, Yuli ^{[1
]}

Qu, Jingping ^{[1
]}

Song, Yuming ^{[1
]}

机构：

[1] Dalian Univ Technol, Sch Pharmaceut Sci & Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 21期

基金：

中国国家自然科学基金;

关键词：

ISATIN-DERIVED KETIMINES; N-BOC KETIMINES; HIGHLY ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; MANNICH REACTION; QUATERNARY STEREOCENTERS; 3-SUBSTITUTED OXINDOLES; TERTIARY STEREOCENTERS; NATURAL-PRODUCTS; NITROOLEFINS;

D O I：

10.1021/acs.orglett.5b02470

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient and practical one-pot sequential process, consisting of an organocatalytic enantioselective Friedel-Crafts-type addition of 4-nonsubstituted pyrazolones to isatin-derived N-Boc ketimines and a subsequent diastereoselective fluorination of the pyrazolone moiety, is developed. This reaction sequence delivers novel oxindole pyrazolone adducts featuring vicinal tetrasubstituted stereocenters with a 0.5 mol % catalyst loading in high yield with excellent enantio- and diastereocontrol. Notably, chloro, bromo, and thioether functionalities can be readily incorporated, rendering a broad diversity of the product.

引用

页码：5168 / 5171

页数：4

共 67 条

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