PEPTIDE-METAL COMPLEX AS AN ASYMMETRIC CATALYST - A CATALYTIC ENANTIOSELECTIVE CYANOHYDRIN SYNTHESIS

被引：71

作者：

MORI, A

NITTA, H

KUDO, M

INOUE, S

机构：

[1] Department of Synthetic Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 34期

关键词：

PEPTIDE-METAL COMPLEX; TITANIUM ALKOXIDE; ENANTIOSELECTIVE; CYANOHYDRIN; ASYMMETRIC CATALYST;

D O I：

10.1016/S0040-4039(00)92163-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An acyclic dipeptide ester, 2-hydroxyl-1-naphthylideneimino-(S)-valyl-(S)-tryptophane methyl ester (1a: Nap-S-Val-S-Trp-OMe), whose terminal amino group is modified to a Schiff base, is designed as a chiral auxiliary of an asymmetric catalyst. The mixture of 1 with titanium alkoxide catalyzes enantioselective hydrocyanation of benzaldehyde to afford optically active (R)-mandelonitrile with stereoselectivities up to 94:6.

引用

收藏

页码：4333 / 4336

页数：4

相关论文

共 20 条

[1] PHOTOREGULATION OF PERMEABILITY ACROSS A MEMBRANE FROM A GRAFT COPOLYMER CONTAINING A PHOTORESPONSIVE POLYPEPTIDE BRANCH [J].

AOYAMA, M ;

WATANABE, J ;

INOUE, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) :5542-5545

[2]

Coppola GM, 1987, ASYMMETRIC SYNTHESIS

[3] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[4] DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX [J].

COREY, EJ ;

IMAI, N ;

ZHANG, HY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :728-729

[5] BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].

EVANS, DA ;

WOERPEL, KA ;

HINMAN, MM ;

FAUL, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728

[6] STEREOSELECTIVE ADDITION OF CYANIDE ION TO CHIRAL RHENIUM PI-ALDEHYDE COMPLEXES OF THE FORMULAS [(ETA-5-C5H5)RE(NO)(PPH3)(ETA-2-O=CHR)]+BF4- - A NEW SYNTHESIS OF OPTICALLY-ACTIVE CYANOHYDRIN DERIVATIVES [J].

GARNER, CM ;

FERNANDEZ, JM ;

GLADYSZ, JA .

TETRAHEDRON LETTERS, 1989, 30 (30) :3931-3934

[7] ASYMMETRIC SYNTHESIS OF BICYCLIC INTERMEDIATES OF NATURAL PRODUCT CHEMISTRY [J].

HAJOS, ZG ;

PARRISH, DR .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1615-1621

[8] ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF SOME ALDEHYDES PROMOTED BY MODIFIED SHARPLESS CATALYST [J].

HAYASHI, M ;

MATSUDA, T ;

OGUNI, N .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (19) :1364-1365

[9] ENANTIOSELECTIVE ADDITION-REACTION OF TRIMETHYLSILYL CYANIDE WITH ALDEHYDES USING A CHIRAL TIN(II) LEWIS ACID [J].

KOBAYASHI, S ;

TSUCHIYA, Y ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1991, (04) :541-544

[10]

MCINTIRE FC, 1949, J AM CHEM SOC, V69, P1377