Enantioselective synthesis of mixed 3,3′-bisindoles via a phosphine-catalyzed umpolung γ-addition of 3′-indolyl-3-oxindoles to allenoates

被引：15

作者：

Tasdan, Yildiz ^{[1
]}

Mei, Guang-Jian ^{[1
]}

Lu, Yixin ^{[1
,2
,3
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

[2] Tianjin Univ, Joint Sch Natl Univ Singapore & Tianjin Univ, Int Campus, Fuzhou 359297, Peoples R China

[3] Natl Univ Singapore Suzhou, Res Inst, Suzhou Ind Pk, Suzhou 215123, Peoples R China

来源：

SCIENCE BULLETIN | 2020年 / 65卷 / 07期

基金：

新加坡国家研究基金会; 中国国家自然科学基金;

关键词：

Umpolung gamma-addition; Amino acid-derived bifunctional phosphine; Allenoates; Mixed 3,3 '-Bisindole; Formal total syntheses; MORITA-BAYLIS-HILLMAN; CARBON QUATERNARY STEREOCENTERS; ASYMMETRIC MICHAEL ADDITION; CONCISE TOTAL-SYNTHESIS; PREPARING EPIDITHIODIOXOPIPERAZINES; SPIRO-EPOXYOXINDOLES; STEREOGENIC CENTERS; GENERAL-APPROACH; 3+2 ANNULATION; CONSTRUCTION;

D O I：

10.1016/j.scib.2020.01.017

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

An enantioselective umpolung gamma-addition reaction of 3'-indolyl-3-oxindoles to allenoates catalyzed by amino acid-derived bifunctional phosphine catalysts has been developed. A wide range of chiral mixed 3,3'-bisindole scaffolds containing an all-carbon quaternary stereogenic center were obtained in high yields and with excellent enantioselectivities. 3,3'-Bisindoles are valuable synthetic intermediates, the employment of which led to formal total syntheses of (+)-Chimonanthine, (+)-Folicanthine and (-)-Calycanthine, as well as facile creation of useful pyrrolidinoindoline core structure. (C) 2020 Science China Press. Published by Elsevier B.V. and Science China Press. All rights reserved.

引用

页码：557 / 563

页数：7

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