Pd-catalyzed enantioselective allylic substitution: New strategic options for the total synthesis of natural products

被引：160

作者：

Graening, T ^{[1
]}

Schmalz, HG ^{[1
]}

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 23期

关键词：

asymmetric synthesis; desymmetrization; homogeneous catalysis; natural products; palladium;

D O I：

10.1002/anie.200301644

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

As versatile as Nature: Pd-catalyzed enantioselective allylic substitution is a powerful reaction in modern synthetic chemistry. The reactions of cyclic allylic substrates (see figure) have recently been proven to be of particular value as they lead to novel and highly efficient strategies in the total synthesis of various natural products.

引用

页码：2580 / 2584

页数：5

共 30 条

[1] Bergner EJ, 2000, EUR J ORG CHEM, V2000, P419, DOI 10.1002/(SICI)1099-0690(200002)2000:3<419::AID-EJOC419>3.0.CO
[2] 2-N
[3] Enantioselective synthesis of (+)-juvabione
Bergner, EJ
Helmchen, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) : 5072 - 5074
[4] Morphine, the Proteus of organic molecules
Blakemore, PR
White, JD
[J]. CHEMICAL COMMUNICATIONS, 2002, (11) : 1159 - 1168
[5] A new approach to (-)-swainsonine by ruthenium-catalyzed ring rearrangement
Buschmann, N
Rückert, A
Blechert, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) : 4325 - 4329
[6] ENANTIOSELECTIVE PALLADIUM CATALYZED ALLYLIC SUBSTITUTION WITH THIENYL OXAZOLINE LIGANDS
FROST, CG
WILLIAMS, JMJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (12) : 2015 - 2018
[7] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE METAL-COMPLEXES
HAYASHI, T
[J]. PURE AND APPLIED CHEMISTRY, 1988, 60 (01) : 7 - 12
[8] Enantioselective palladium-catalyzed allylic substitutions with asymmetric chiral ligands
Helmchen, G
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) : 203 - 214
[9] A new and general synthetic pathway to Strychnos indole alkaloids:: Total syntheses of (-)-dehydrotubifoline and (-)-tubifoline by palladium-catalyzed asymmetric allylic substitution
Mori, M
Nakanishi, M
Kajishima, D
Sato, Y
[J]. ORGANIC LETTERS, 2001, 3 (12) : 1913 - 1916
[10] Morphine synthesis and biosynthesis - An update
Novak, BH
Hudlicky, T
Reed, JW
Mulzer, J
Trauner, D
[J]. CURRENT ORGANIC CHEMISTRY, 2000, 4 (03) : 343 - 362

← 1 2 3 →