Novel thiazolidine derivatives as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes

被引：23

作者：

Meng, QL ^{[1
]}

Li, YL ^{[1
]}

He, Y ^{[1
]}

Guan, YD ^{[1
]}

机构：

[1] Peking Univ, Dept Chem, Beijing 100871, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 21期

关键词：

D O I：

10.1016/S0957-4166(00)00391-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New chiral thiazolidine derivatives were synthesized conveniently from natural L-cysteine and showed good enantioselectivity (up to 90% ee) in the addition of diethylzinc to aldehydes. The catalytic efficiency of the thiazolidine derivatives is influenced by the different structures of the thiazolidine rings and the bulkiness of R moiety in the ester groups. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4255 / 4261

页数：7

共 10 条

[1] Enantioselective addition of Et(2)Zn to aldehydes promoted by a chiral Schiff base metal complex [J].

Cozzi, PG ;

Papa, A ;

UmaniRonchi, A .

TETRAHEDRON LETTERS, 1996, 37 (26) :4613-4616

[2] New delta-aminoalcohol for the enantioselective addition of dialkylzincs to aldehydes [J].

Genov, M ;

Dimitrov, V ;

Ivanova, V .

TETRAHEDRON-ASYMMETRY, 1997, 8 (22) :3703-3706

[3] SULFUR DERIVATIVES OF EPHEDRA ALKALOIDS - NEW AND HIGHLY EFFICIENT CHIRAL CATALYSTS [J].

HOF, RP ;

POELERT, MA ;

PEPER, NCMW ;

KELLOGG, RM .

TETRAHEDRON-ASYMMETRY, 1994, 5 (01) :31-34

[4]

Huang HL, 1996, TETRAHEDRON-ASYMMETR, V7, P3067

[5] CATALYTIC ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES [J].

KITAMURA, M ;

SUGA, S ;

KAWAI, K ;

NOYORI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :6071-6072

[6] Enantioselective addition of diethylzinc to aldehydes using 2-azanorbornylmethanols and 2-azanorbornylmethanethiol as a catalyst [J].

Nakano, H ;

Kumagai, N ;

Matsuzaki, H ;

Kabuto, C ;

Hongo, H .

TETRAHEDRON-ASYMMETRY, 1997, 8 (09) :1391-1401

[7] ASYMMETRIC REDUCTION OF ALPHA,BETA-UNSATURATED KETONES WITH CHIRAL HYDRIDE REAGENTS PREPARED FROM LITHIUM ALUMINUM-HYDRIDE AND (S)-4-ANILINO-3-METHYLAMINO-1-BUTANOL AND (S)-4-(2,6-XYLIDINO)-3-METHYLAMINO-1-BUTANOL [J].

SATO, T ;

GOTOH, Y ;

WAKABAYASHI, Y ;

FUJISAWA, T .

TETRAHEDRON LETTERS, 1983, 24 (38) :4123-4126

[8] ENANTIOSELECTIVE ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES [J].

SOAI, K ;

NIWA, S .

CHEMICAL REVIEWS, 1992, 92 (05) :833-856

[9] CHIRAL N,N-DIALKYLNOREPHEDRINES AS CATALYSTS OF THE HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALIPHATIC AND AROMATIC-ALDEHYDES - THE ASYMMETRIC-SYNTHESIS OF SECONDARY ALIPHATIC AND AROMATIC ALCOHOLS OF HIGH OPTICAL PURITY [J].

SOAI, K ;

YOKOYAMA, S ;

HAYASAKA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4264-4268

[10] Sulfur-containing beta-amino alcohols as catalysts in enantioselective synthesis [J].

Trentmann, W ;

Mehler, T ;

Martens, J .

TETRAHEDRON-ASYMMETRY, 1997, 8 (12) :2033-2043

← 1 →