Palladium-catalyzed allylic alkylation of tert-butyl(diphylmethylene)-glycinate with simple allyl esters under chiral phase transfer conditions

被引：160

作者：

Chen, GS

Deng, YJ ^{[1
]}

Gong, LZ

Mi, AQ

Cui, X

Jiang, YZ

Choi, MCK

Chan, ASC

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Union Lab Asymmetr Synth, Chengdu 610041, Peoples R China

[2] Hong Kong Polytech Univ, Open Lab Chriotechnol, Hong Kong, Hong Kong, Peoples R China

[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 11期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/S0957-4166(01)00276-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first example of palladium-catalyzed allylic alkylation of,in imino ester with simple allyl esters in the presence of a chiral quaternary ammonium salt is reported. The presence of molecular sieves was found to have a beneficial effect on the enantioselectivity of the reaction by scavenging water from the system. Alkylated products vith e.e.s of up to 61% were obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1567 / 1571

页数：5

共 28 条

[1] Abellán T, 2000, EUR J ORG CHEM, V2000, P2689
[2] ALPHA-AMINO ESTER DERIVATIVES AS NUCLEOPHILES IN STEREOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS
BALDWIN, IC
WILLIAMS, JMJ
BECKETT, RP
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (07) : 1515 - 1518
[3] The direct synthesis of novel enantiomerically pure α-amino acids in protected form via Suzuki cross-coupling
Collier, PN
Campbell, AD
Patel, I
Taylor, RJK
[J]. TETRAHEDRON LETTERS, 2000, 41 (36) : 7115 - 7119
[4] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions
Corey, EJ
Xu, F
Noe, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12414 - 12415
[5] 3,8-diazabicyclo[3.2.1]octan-2-one peptide mimetics: Synthesis of a conformationally restricted inhibitor of farnesyltransferase
Dinsmore, CJ
Bergman, JM
Bogusky, MJ
Culterson, JC
Hamilton, KA
Graham, SL
[J]. ORGANIC LETTERS, 2001, 3 (06) : 865 - 868
[6] Design and use of an oxazolidine silyl enol ether as a new homoalanine carbanion equivalent for the synthesis of carbon-linked isosteres of O-glycosyl serine and N-glycosyl asparagine
Dondoni, A
Marra, A
Massi, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) : 933 - 944
[7] BIS(OXAZOLINE) COPPER-COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS
EVANS, DA
FAUL, MM
BILODEAU, MT
ANDERSON, BA
BARNES, DM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) : 5328 - 5329
[8] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION
GAO, Y
HANSON, RM
KLUNDER, JM
KO, SY
MASAMUNE, H
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) : 5765 - 5780
[9] SYNTHESIS OF ALPHA-AMINO-ACIDS USING TRANSITION-METAL CATALYSIS-ALKYLATION OF SCHIFF-BASES DERIVED FROM ALPHA - AMINO-ACID ESTERS (REGIO, STEREO - SELECTIVITY
GENET, JP
JUGE, S
ACHI, S
MALLART, S
MONTES, JR
LEVIF, G
[J]. TETRAHEDRON, 1988, 44 (17) : 5263 - 5275
[10] ENANTIOSELECTIVITY IN ORGANO TRANSITION-METAL CHEMISTRY - AN UNPRECEDENTED LIGAND EFFECT IN PI-ALLYL PALLADIUM CHEMISTRY
GENET, JP
JUGE, S
MONTES, JR
GAUDIN, JM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (11) : 718 - 719

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