Palladium-catalyzed asymmetric alkylation of 2-azaallyl acetates for the synthesis of β-carboxyaspartic acid derivatives

被引：9

作者：

Yamaguchi, M ^{[1
]}

Ohba, K ^{[1
]}

Tomonaga, H ^{[1
]}

Yamagishi, T ^{[1
]}

机构：

[1] Tokyo Metropolitan Univ, Dept Appl Chem, Grad Sch Engn, Hachioji, Tokyo 1920397, Japan

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 1999年 / 140卷 / 03期

关键词：

asymmetric alkylation; palladium catalyst; 2-Azaallyl acetate; beta-carboxyaspartic acid derivatives;

D O I：

10.1016/S1381-1169(98)00237-4

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Palladium-catalyzed asymmetric alkylation of 2-azaallyl acetate, N-(diphenylmethylene)acetoxyglycine ester with a sodium salt of malonate ester was successfully carried out. High enantioselectivities were achieved using sodium dimethyl methylmalonate (98%ee) or sodium dimethyl malonate (93%ee) as a nucleophile with t-butyl ester of 2-azaallyl acetate in the presence of (S)-BINAP in acetonitrile. (C) 1999 Elsevier Science B.V. All rights reserved.

引用

页码：255 / 258

页数：4

共 50 条

[41] Palladium-catalyzed synthesis of 3-indolecarboxylic acid derivatives
Soederberg, Bjoern C. G.
Banini, Serge R.
Turner, Michael R.
Minter, Aaron R.
Arrington, Amanda K.
SYNTHESIS-STUTTGART, 2008, (06): : 903 - 912
[42] Palladium-catalyzed synthesis of quinoxaline derivatives
Wallace, Jeffery M.
Soederberg, Bjoern C. G.
Tamariz, Joaquin
Akhmedov, Novruz G.
Hurley, Mathew T.
TETRAHEDRON, 2008, 64 (41) : 9675 - 9684
[43] Effective synthesis of bicyclodienes via palladium-catalyzed asymmetric allylic alkylation and ruthenium-catalyzed cycloisomerization
Havare, Nizam
TURKISH JOURNAL OF CHEMISTRY, 2020, 44 (06) : 1445 - +
[44] Palladium-Catalyzed Asymmetric Synthesis of 2-Alkynyl Oxacycles
Daniels, David S. B.
Thompson, Amber L.
Anderson, Edward A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) : 11506 - 11510
[45] Synthesis of 2-substituted benzofuran derivatives by the palladium-catalyzed intermolecular coupling of 2-fluoroallylic acetates with phenols
Udagawa, Takumi
Kogawa, Masaki
Tsuchi, Yukiko
Watanabe, Hirotaka
Yamamoto, Mitsuaki
Kawatsura, Motoi
TETRAHEDRON LETTERS, 2017, 58 (03) : 227 - 230
[46] SYNTHESIS OF VINYLSILANES BY PALLADIUM-CATALYZED REACTION OF TRIMETHYLSILYLALLYL ACETATES WITH NUCLEOPHILES
HIRAO, T
ENDA, J
OHSHIRO, Y
AGAWA, T
TETRAHEDRON LETTERS, 1981, 22 (32) : 3079 - 3080
[47] Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides
Katcher, Matthew H.
Doyle, Abigail G.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (49) : 17402 - 17404
[48] The asymmetric synthesis of cyclopentane derivatives by palladium-catalyzed coupling of prochiral alkylboron compounds
Cho, SY
Shibasaki, M
TETRAHEDRON-ASYMMETRY, 1998, 9 (21) : 3751 - 3754
[49] Enantioselective Synthesis of Hydrindanes via Palladium-Catalyzed Asymmetric Desymmetrization of Cyclohexadiene Derivatives
Wu, Shu
Li, Miaomiao
Lu, Jiajun
Yang, Chi
Huang, Yue
Lin, Aijun
ORGANIC LETTERS, 2025, 27 (06) : 1422 - 1427
[50] Palladium-Catalyzed Asymmetric Allylic Alkylation of 2-Acylimidazoles as Ester Enolate Equivalents
Trost, Barry M.
Lehr, Konrad
Michaelis, David J.
Xu, Jiayi
Buckl, Andreas K.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) : 8915 - +

← 1 2 3 4 5 →