Bis(ethylsulfonamide)amines via nucleophilic ring-opening of chiral aziridines. Application to Ti-mediated addition of diethylzinc to benzaldehyde

被引：49

作者：

Cernerud, M ^{[1
]}

Skrinning, A ^{[1
]}

Bergere, I ^{[1
]}

Moberg, C ^{[1
]}

机构：

[1] ROYAL INST TECHNOL,DEPT CHEM,SE-10044 STOCKHOLM,SWEDEN

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 20期

基金：

瑞典研究理事会;

关键词：

D O I：

10.1016/S0957-4166(97)00410-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Homochiral bis(N-triflyl-2-alkyl-2-aminoethyl)amines obtained from N-triflyl-2-alkylaziridines via reaction with benzylamine, catalyze the titanium-mediated addition of diethylzinc to benzaldehyde to yield 1-phenylpropanol in up to 78% ee in the presence of molecular sieves. Use of tetradentate analogs prepared by reaction of the aziridine with 2-(aminomethyl)pyridine or 2-aminophenol resulted in lower enantioselectivity. (C) 1997 Elsevier Science Ltd.

引用

页码：3437 / 3441

页数：5

共 25 条

[1] New ligands for the titanium(IV)-induced asymmetric reduction of ketones with catecholborane
Almqvist, F
Torstensson, L
Gudmundsson, A
Frejd, T
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (04): : 376 - 377
[2] SYNTHESIS AND CHARACTERIZATION OF A SERIES OF ACHIRAL AND CHIRAL MONO[(DIEN)PT(II)I]I AND BIS[(DIEN)PT(II)I]I DERIVATIVES AS POTENTIAL DNA AND RNA STRUCTURE PROBES AND ANTICANCER DRUGS
ALUL, R
CLEAVER, MB
TAYLOR, JS
[J]. INORGANIC CHEMISTRY, 1992, 31 (17) : 3636 - 3646
[3] BERRY MB, 1992, SYNLETT, P41
[4] SELECTIVITY AND MECHANISM IN CATALYTIC ASYMMETRIC-SYNTHESIS
BROWN, JM
[J]. CHEMICAL SOCIETY REVIEWS, 1993, 22 (01) : 25 - 41
[5] C-3-symmetric tripodal tetra-amines - preparation from chiral amino alcohols via aziridines
Cernerud, M
Adolfsson, H
Moberg, C
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (15) : 2655 - 2662
[6] CHIRAL TITANIUM COMPLEXES FOR ENANTIOSELECTIVE ADDITION OF NUCLEOPHILES TO CARBONYL GROUPS
DUTHALER, RO
HAFNER, A
[J]. CHEMICAL REVIEWS, 1992, 92 (05) : 807 - 832
[7] 2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES
FUKUYAMA, T
JOW, CK
CHEUNG, M
[J]. TETRAHEDRON LETTERS, 1995, 36 (36) : 6373 - 6374
[8] GAUSS W, 1952, HELV CHIM ACTA, V35, P2359
[9] PROCEDURE FOR THE CATALYTIC ASYMMETRIC EPOXIDATION OF ALLYLIC ALCOHOLS IN THE PRESENCE OF MOLECULAR-SIEVES
HANSON, RM
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) : 1922 - 1925
[10] PREPARATION AND ABSORPTION AND CIRCULAR-DICHROISM SPECTRA OF COBALT(III) COMPLEXES WITH N,N,N',N'-TETRAKIS(2-AMINOETHYL)-1,2-ETHANEDIAMINE, 1,3-PROPANEDIAMINE, 1,4-BUTANEDIAMINE, AND (R,R) AND (R,S) 2,4-PENTANEDIAMINE
HATA, K
DOH, MK
KASHIWABARA, K
FUJITA, J
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (01) : 190 - 195

← 1 2 3 →