Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center

被引：90

作者：

Takizawa, Shinobu ^{[1
]}

Kishi, Kenta ^{[1
]}

Yoshida, Yasushi ^{[1
]}

Mader, Steffen ^{[2
]}

Arteaga, Fernando Arteaga ^{[1
]}

Lee, Shoukou ^{[3
]}

Hoshino, Manabu ^{[3
]}

Rueping, Magnus ^{[2
]}

Fujita, Makoto ^{[3
]}

Sasai, Hiroaki ^{[1
]}

机构：

[1] Osaka Univ, Inst Sci & Ind Res ISIR, Ibaraki, Osaka 5670047, Japan

[2] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

[3] Univ Tokyo, Sch Engn, Dept Appl Chem, Tokyo 1138656, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 51期

关键词：

allenes; annulations; organocatalysis; phosphines; umpolung; RAUHUT-CURRIER REACTION; BAYLIS-HILLMAN REACTION; ENANTIOSELECTIVE 4+1 ANNULATIONS; GAMMA-SUBSTITUENT ALLENOATES; C; N-CYCLIC AZOMETHINE IMINES; ASYMMETRIC 3+2 CYCLOADDITION; ELECTRON-DEFICIENT OLEFINS; HILIMAN REACTION; EFFICIENT METHOD; SEQUENTIAL 2+3;

D O I：

10.1002/anie.201508022

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed beta,gamma-umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence, involving oxy-Michael and Rauhut-Currier reactions, produced highly functionalized tetrahydrobenzofuranones, bearing a chiral tetrasubstituted stereogenic center, in up to 96% ee.

引用

页码：15511 / 15515

页数：5

共 35 条

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