Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles

被引：48
|
作者：
Chen, Lili [1 ]
Shen, Jun-Jian [1 ]
Gao, Qian [1 ]
Xu, Senmiao [1 ,2 ]
机构：
[1] Chinese Acad Sci, Univ Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat,Suzhou Re, Lanzhou Inst Chem Phys,Ctr Excellence Mol Synth, Lanzhou 730000, Gansu, Peoples R China
[2] Hangzhou Normal Univ, Minist Educ, Key Lab Organosilicon Chem & Mat Technol, Hangzhou 311121, Zhejiang, Peoples R China
来源：
CHEMICAL SCIENCE | 2018年 / 9卷 / 26期
基金：
中国国家自然科学基金;
关键词：
TERTIARY BORONIC ESTERS; AMINOBORONIC ACID-DERIVATIVES; ENANTIOSELECTIVE SYNTHESIS; REGIOSELECTIVE 1,4-HYDROBORATION; PINACOLBORYL ADDITION; MULTIPLE-MYELOMA; PYRIDINES; HYDROBORATION; CONSTRUCTION; SILABORATION;
D O I：
10.1039/c8sc01815d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A copper(i)-catalyzed dearomative borylation of N-alkoxycarbonyl protected indole-3-carboxylates has been developed. The boron addition in this reaction occurred regioselectively at the 2-position of indoles followed by diastereoselective protonation, affording the corresponding stable cyclic chiral -amino boronates (2-borylindolines) in moderate to good yields with excellent diastereo- and enantioselectivities. The product 2c could be used as a versatile precursor to undergo subsequent stereoselective transformations, delivering highly functionalized 2,3,3-trisubstituted chiral indolines.
引用
收藏
页码：5855 / 5859
页数：5
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