Revisiting optically active quaternary derivatives made from prolinol as phase transfer catalysts

被引：17

作者：

Dehmlow, EV ^{[1
]}

Klauck, R ^{[1
]}

Düttmann, S ^{[1
]}

Neumann, B ^{[1
]}

Stammler, HG ^{[1
]}

机构：

[1] Univ Bielefeld, Fak Chem, D-33501 Bielefeld, Germany

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(98)00213-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New non-racemic ammonium salts derived from prolinol have been prepared which are stereogenic both at N and at C. Absolute configurations rest on X-ray structures for 3c and 7a. The new compounds have been tested in a number of known enantioselective phase transfer catalytic (PTC) reactions to gain insight into steric control factors in such processes. Only very moderate e.e.s were observed. A SAMP hydrazone related catalyst (7a) reported by other authors was fully characterized. Racemic reaction products were obtained in two alkylations of diphenylmethylene benzylimine in the presence of this pure catalyst 7a. Very high e.e.s reported previously by others could not be reproduced. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2235 / 2244

页数：10

共 24 条

[1] AVARO M, 1969, J CHEM SOC CHEM COMM, P445
[2] ASYMMETRIC INDUCTION IN BOROHYDRIDE REDUCTION OF CARBONYL-COMPOUNDS BY MEANS OF CHIRAL PHASE-TRANSFER CATALYSTS .2.
COLONNA, S
FORNASIER, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (04): : 371 - 373
[3] GENERATION AND SYNTHETIC USE OF METALLATED DIMETHYLHYDRAZONES REGION AND STEREOSELECTIVE ALKYLATION OF CARBONYL-COMPOUNDS
COREY, EJ
ENDERS, D
[J]. CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (04): : 1337 - 1361
[4] CHIRAL CROWN COMPLEXES CATALYZE MICHAEL ADDITION-REACTIONS TO GIVE ADDUCTS IN HIGH OPTICAL YIELDS
CRAM, DJ
SOGAH, GDY
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (13) : 625 - 628
[5] Dehmlow E. V., 1993, Phase Transfer Catalysis
[6] APPLICATIONS OF PHASE TRANSFER CATALYSIS .4. HALOGEN EXCHANGE AND REACTIVITIES OF DIBROMOCARBENE, CHLOROBROMOCARBENE AND DICHLOROCARBENE
DEHMLOW, EV
LISSEL, M
HEIDER, J
[J]. TETRAHEDRON, 1977, 33 (03) : 363 - 366
[7] DEHMLOW EV, 1994, POL J CHEM, V68, P2199
[8] DEHMLOW EV, 1992, LIEBIGS ANN CHEM, P283
[9] APPLICATIONS OF PHASE-TRANSFER CATALYSIS .39. DO SIMPLE OPTICALLY-ACTIVE PHASE-TRANSFER AGENTS CATALYZE ENANTIOSELECTIVE ETHER FORMATION
DEHMLOW, EV
SLEEGERS, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) : 3875 - 3877
[10] DEHMLOW EV, 1981, J CHEM RES-S, P292

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