Enantioselective Pd-catalyzed allylic alkylation of Indoles by a new class of chiral ferrocenyl P/S Ligands

被引：119

作者：

Cheung, Hong Yee ^{[1
]}

Yu, Wing-Yiu ^{[1
]}

Lam, Fuk Loi ^{[1
]}

Au-Yeung, Terry T. -L. ^{[1
]}

Zhou, Zhongyuan ^{[1
]}

Chan, Tak Hang ^{[1
]}

Chan, Albert S. C. ^{[1
]}

机构：

[1] Hong Kong Polytech Univ, Inst Mol Technol Drug Discovery & Synthes, Open Lab Chirotechnol, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 21期

关键词：

D O I：

10.1021/ol7018532

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral ferrocenyl heterobidentate P/S ligands bearing both central and planar chirality were prepared from (S)-Ugi's amine via a three-step modular synthesis. Through systematic screening and optimization, L8 was found to be the best ligand for Pd-catalyzed asymmetric allylic alkylation of indoles with ee's up to 96% being attained.

引用

页码：4295 / 4298

页数：4

共 25 条

[1] Highly enantioselective synthesis of tetrahydro-β-carbolines and tetrahydro-γ-carbolines via Pd-catalyzed intramolecular allylic alkylation
Bandini, M
Melloni, A
Piccinelli, F
Sinisi, R
Tommasi, S
Umani-Ronchi, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) : 1424 - 1425
[2] New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic subsitution: Controlling the regioselectivity
Bandini, M
Melloni, A
Umani-Ronchi, A
[J]. ORGANIC LETTERS, 2004, 6 (18) : 3199 - 3202
[3] Can simple enones be useful partners for the catalytic stereoselective alkylation of indoles?
Bandini, M
Fagioli, M
Garavelli, M
Melloni, A
Trigari, V
Umani-Ronchi, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22) : 7511 - 7518
[4] β-phenylethylamines and the isoquinoline alkaloids
Bentley, KW
[J]. NATURAL PRODUCT REPORTS, 2004, 21 (03) : 395 - 424
[5] Highly enantioselective copper(I)-fesulphos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides
Cabrera, S
Arrayás, RG
Carretero, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) : 16394 - 16395
[6] Nickel-catalyzed asymmetric α-arylation of ketone enolates
Chen, GS
Kwong, FY
Chan, HO
Yu, WY
Chan, ASC
[J]. CHEMICAL COMMUNICATIONS, 2006, (13) : 1413 - 1415
[7] Application of chiral mixed phosphorus/sulfur ligands to enantioselective rhodium-catalyzed dehydroamino acid hydrogenation and ketone hydrosilylation processes
Evans, DA
Michael, FE
Tedrow, JS
Campos, KR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) : 3534 - 3543
[8] Application of chiral mixed phosphorus/sulfur ligands to palladium-catalyzed allylic substitutions
Evans, DA
Campos, KR
Tedrow, JS
Michael, FE
Gagné, MR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) : 7905 - 7920
[9] GOKEL GW, 1972, J ORG CHEM, V37, P3052, DOI 10.1021/jo00985a002
[10] Catalytic asymmetric alkynylation of α-imino ester:: A versatile approach to optically active unnatural α-amino acid derivatives
Ji, JX
Wu, J
Chan, ASC
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (32) : 11196 - 11200

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