Novel potential enantioselective phase transfer catalysts based on lupinine

被引：3

作者：

Dehmlow, EV ^{[1
]}

Klauck, R ^{[1
]}

Neumann, B ^{[1
]}

Stammler, HG ^{[1
]}

机构：

[1] Univ Bielefeld, Fak Chem, D-33615 Bielefeld, Germany

来源：

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1998年 / 340卷 / 06期

关键词：

D O I：

10.1002/prac.19983400612

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Ten N-alkylated lupininium derivatives 5-8 were prepared as potential enantioselective phase transfer catalysts. Compounds 5a-d, 6a-d contain four asymmetric centers (including one in the side chain) with known configuration resting on an X-ray structure. Preliminary PT catalytic experiments in several reactions gave high chemical yields but relatively disappointing enantioselectivities.

引用

页码：572 / 575

页数：4

共 16 条

[1] SYNTHESES FROM LUPININE [J].

CLEMO, GR ;

RUDINGER, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1951, (OCT) :2714-2718

[2] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].

Corey, EJ ;

Xu, F ;

Noe, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415

[3]

Dehmlow E. V., 1993, Phase Transfer Catalysis

[4]

DEHMLOW EV, 1998, IN PRESS TETRAHEDRON

[5]

Esikova I.A., 1997, ACS SYM SER, V659, P89

[6]

Goldberg Y, 1992, Phase Transfer Catalysis: Selected Problems and Applications

[7]

HERMANN K, 1977, J ORG CHEM, V44, P2208

[8]

JULIA S, 1981, J CHEM SOC PERK T 1, P574, DOI 10.1039/p19810000574

[9] On lupinin [J].

Karrer, P ;

Canal, F ;

Zohner, K ;

Widmer, R .

HELVETICA CHIMICA ACTA, 1928, 11 :1062-1084

[10] STRUCTURE OF ALKALOID LUPININE [J].

KOZIOL, A ;

KOSTURKIEWICZ, Z ;

PODKOWINSKA, H .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1978, 34 (NOV) :3491-3494

← 1 2 →