Palladium-catalyzed enantioselective domino reaction for the efficient synthesis of vitamin E

被引：135

作者：

Tietze, LF ^{[1
]}

Sommer, KM ^{[1
]}

Zinngrebe, J ^{[1
]}

Stecker, F ^{[1
]}

机构：

[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 02期

关键词：

asymmetric catalysis; domino reactions; Heck reactions; palladium; vitamins; Wacker oxidation;

D O I：

10.1002/anie.200461629

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new route to vitamin E: The palladium-catalyzed enantioselective domino reaction of the unsaturated phenol derivative 1 with acrylate provides efficient access to the chiral chroman 2 with 96% ee and in 84% yield (see scheme). Intermediate 2 can then be converted into vitamin E in a few steps.

引用

页码：257 / 259

页数：3

共 50 条

[1] Enantioselective palladium-catalyzed total synthesis of vitamin E by employing a domino Wacker-Heck reaction
Tietze, Lutz F.
Stecker, Florian
Zinngrebe, Julia
Sommer, Konrad M.
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (34) : 8770 - 8776
[2] Palladium-catalyzed Domino-Wacker-carbonylation reaction for the enantioselective synthesis of chromans and benzodioxins
Tietze, Lutz F.
Zinngrebe, Julia
Spiegl, Dirk A.
Stecker, Florian
HETEROCYCLES, 2007, 74 : 473 - 489
[3] Total Synthesis of Linoxepin through a Palladium-Catalyzed Domino Reaction
Tietze, Lutz F.
Duefert, Svenia-C.
Clerc, Jerome
Bischoff, Matthias
Maass, Christian
Stalke, Dietmar
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) : 3191 - 3194
[4] Palladium-Catalyzed, Enantioselective Heine Reaction
Punk, Molly
Merkley, Charlotte
Kennedy, Katlyn
Morgan, Jeremy B.
ACS CATALYSIS, 2016, 6 (07): : 4694 - 4698
[5] Palladium-catalyzed enantioselective Heine reaction
Kennedy, Katlyn
Punk, Molly
Merkley, Charlotte
Morgan, Jeremy
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[6] First total synthesis of (±)-Linoxepin via a palladium-catalyzed domino reaction
Schild, Svenia C.
Clerc, Jerme
Tietze, Lutz F.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[7] Palladium-catalyzed enantioselective synthesis of carbanucleosides
Trost, BM
Madsen, R
Guile, SD
Brown, B
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (25) : 5947 - 5956
[8] Palladium-Catalyzed Enantioselective Heteroarenyne Cycloisomerization Reaction
Zhao, Ping
Luan, Xinjun
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (06) : 2520 - 2521
[9] Palladium-Catalyzed Enantioselective Heteroarenyne Cycloisomerization Reaction
Liang, Ren-Xiao
Song, Ling-Jie
Lu, Jin-Bo
Xu, Wei-Yan
Ding, Chao
Jia, Yi-Xia
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (13) : 7412 - 7417
[10] Enantioselective Palladium-Catalyzed Dearomative Cyclization for the Efficient Synthesis of Terpenes and Steroids
Du, Kang
Guo, Pan
Chen, Yuan
Cao, Zhen
Wang, Zheng
Tang, Wenjun
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (10) : 3033 - 3037

← 1 2 3 4 5 →