Novel ligands derived from S-tyrosine for the enantioselective addition of diethylzinc to aldehydes

被引：41

作者：

Beliczey, J ^{[1
]}

Giffels, G ^{[1
]}

Kragl, U ^{[1
]}

Wandrey, C ^{[1
]}

机构：

[1] FORSCHUNGSZENTRUM JULICH, FORSCHUNGSZENTRUM, INST BIOTECHNOL, D-52425 JULICH, GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(97)00150-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(S)-2-N,N-dibutylamino-3-butyl-1-[4-(4-phenylmethoxy)-phenyl]heptain-3-ol 3 based on (S)-tyrosine has been synthesised. For the diethylzinc addition to both aliphatic and aromatic aldehydes, high enantiomeric excesses up to 95% were obtained. (C) 1997 Elsevier Science Ltd.

引用

页码：1529 / 1530

页数：2

共 10 条

[1] CATALYTIC ASYMMETRIC ALKYLATION OF ALDEHYDES BY DIETHYLZINC IN THE PRESENCE OF N-ISO-PROPYLEPHEDRINE - DEPENDENCE OF ENANTIOSELECTIVITY ON ET2ZN-RCHO [J].

CHALONER, PA ;

LANGADIANOU, E .

TETRAHEDRON LETTERS, 1990, 31 (36) :5185-5188

[2] SYNTHESIS OF BETA-AMINO ALCOHOLS DERIVED FROM L-VALINE [J].

DELAIR, P ;

EINHORN, C ;

EINHORN, J ;

LUCHE, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4680-4682

[3] NEW BETA-AMINO ALCOHOLS DERIVED FROM L-VALINE AS CHIRAL INDUCTORS FOR ENANTIOSELECTIVE REDUCTIONS OF, AND NUCLEOPHILIC ADDITIONS TO CARBONYL-COMPOUNDS [J].

DELAIR, P ;

EINHORN, C ;

EINHORN, J ;

LUCHE, JL .

TETRAHEDRON, 1995, 51 (01) :165-172

[4] CHANGES OF ENANTIOSELECTIVITY WITH THE SUBSTRATE RATIO FOR THE ADDITION OF DIETHYLZINC TO ALDEHYDES USING A CATALYST COUPLED TO A SOLUBLE POLYMER [J].

DREISBACH, C ;

WISCHNEWSKI, G ;

KRAGL, U ;

WANDREY, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (07) :875-878

[5] NEW SOLID-PHASE CATALYSTS FOR ASYMMETRIC-SYNTHESIS - CROSS-LINKED POLYMERS CONTAINING A CHIRAL SHIFF BASE ZINC COMPLEX [J].

ITSUNO, S ;

SAKURAI, Y ;

ITO, K ;

MARUYAMA, T ;

NAKAHAMA, S ;

FRECHET, JMJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :304-310

[6] ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES PROMOTED BY CHIRAL AMINO-ALCOHOLS - MECHANISM AND NONLINEAR EFFECT [J].

KITAMURA, M ;

OKADA, S ;

SUGA, S ;

NOYORI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4028-4036

[7] Continuous asymmetric synthesis in a membrane reactor [J].

Kragl, U ;

Dreisbach, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (06) :642-644

[8]

Kragl U, 1996, ANGEW CHEM, V108, P684

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

SOAI, K ;

NIWA, S .

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

[10] 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

← 1 →