Rhodium(I)-catalyzed addition of phenols to dienes.: A new convergent synthesis of vitamin E

被引：20

作者：

Bienaymé, H ^{[1
]}

Ancel, JE

Meilland, P

Simonato, JP

机构：

[1] Rhone Poulenc Industrialisat, F-69192 St Fons, France

[2] Rhodia Rech, F-69192 St Fons, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 18期

关键词：

vitamin E; homogeneous catalysis; rhodium; C-alkylation; phenol;

D O I：

10.1016/S0040-4039(00)00381-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly convergent and atom-economical synthesis of (dl)-[alpha]-tocopherol (vitamin E) is proposed, the realization of which was made possible by the discovery of the regioselective Rh(I)-catalyzed arylation of beta-springene with trimethylhydroquinone. Other phenolic compounds and 2-substituted-1,3-dienes were shown to undergo this transformation. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3339 / 3343

页数：5

共 50 条

[31] Easily accessible C2-symmetric chiral bicyclo[3.3.0] dienes as ligands for rhodium-catalyzed asymmetric 1,4-addition [J].

Feng, Chen-Guo ;

Wang, Zhi-Qian ;

Tian, Ping ;

Xu, Ming-Hua ;

Lin, Guo-Qiang .

CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) :1511-1516

[32] A New Type of Chiral Cyclic Sulfinamide-Olefin Ligands for Rhodium-Catalyzed Asymmetric Addition [J].

Wen, Quan ;

Zhang, Li ;

Xiong, Jing ;

Zeng, Qingle .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (32) :5360-5364

[33] Efficient synthesis of vitamin E intermediate by lipase-catalyzed regioselective transesterification [J].

Wei, Chun ;

Fu, Xian-Feng ;

Wang, Zhao ;

Yu, Xin-Jun ;

Zhang, Yin-Jun ;

Zheng, Jian-Yong .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2014, 106 :90-94

[34] Convergent, asymmetric synthesis of vicinal amino alcohols via Rh-catalyzed addition of α-amido trifluoroborates to carbonyls [J].

Buesking, Andrew W. ;

Ellman, Jonathan A. .

CHEMICAL SCIENCE, 2014, 5 (05) :1983-1987

[35] Rhodium(I)-catalyzed [2+2+2] cycloadditions with N-functionalized 1-alkynylamides: A conceptually new strategy for the regiospecific synthesis of substituted indolines [J].

Witulski, B ;

Stengel, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (16) :2426-2430

[36] Synthesis of meta-Arylated Phenol Derivatives by Rhodium(I)-Catalyzed Arylation of Quinone Monoacetal [J].

Huang, Jianhang ;

Liu, Na ;

Lu, Tao ;

Dou, Xiaowei .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (18) :3466-3470

[37] Rhodium(I)-catalyzed intramolecular hydroacylation of 4,6-dienals: Novel synthesis of cycloheptenones [J].

Oonishi, Yoshihiro ;

Mori, Miwako ;

Sato, Yoshihiro .

SYNTHESIS-STUTTGART, 2007, (15) :2323-2336

[38] Synthesis of Functionalized Polycyclic Compounds: Rhodium(I)-Catalyzed Intramolecular Cycloaddition of Yne and Ene Vinylidenecyclopropanes [J].

Lu, Bei-Li ;

Shi, Min .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (50) :12027-12031

[39] Synthesis of Symmetrical and Unsymmetrical 1,4-Dithiins by Rhodium-Catalyzed Sulfur Addition Reaction to Alkynes [J].

Arisawa, Mieko ;

Ichikawa, Takuya ;

Tanii, Saori ;

Yamaguchi, Masahiko .

SYNTHESIS-STUTTGART, 2016, 48 (18) :3107-3119

[40] Regio- and Enantioselective Synthesis of N-Substituted Pyrazoles by Rhodium-Catalyzed Asymmetric Addition to Allenes [J].

Haydl, Alexander M. ;

Xu, Kun ;

Breit, Bernhard .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (24) :7149-7153

← 1 2 3 4 5 →