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
收藏
页码：5168 / 5171
页数：4
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