MECHANISTIC STUDIES ON THE ASYMMETRIC ADDITION OF HCN TO ALDEHYDES CATALYZED BY CYCLO[(S)-HIS-(S)-PHE]

被引：17

作者：

HOGG, DJP ^{[1
]}

NORTH, M ^{[1
]}

机构：

[1] UNIV WALES,DEPT CHEM,BANGOR LL57 2UW,GWYNEDD,WALES

来源：

TETRAHEDRON | 1993年 / 49卷 / 05期

关键词：

CYCLO[(S)-PHENYLALANYL-(S)-HISTIDYL; CONFORMATION; HYDROCYANATION; ASYMMETRIC; MECHANISM;

D O I：

10.1016/S0040-4020(01)86289-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The nature of the interaction between HCN and cyclol(S)-His-(S)-Phe] during the asymmetric hydrocyanation of benzaldehyde is investigated by variable pH nmr spectroscopy. The structure of the protonated form of cyclo[(S)-His-(S)-Phe] is determined by variable temperature NMR and molecular mechanics calculations.

引用

收藏

页码：1079 / 1090

页数：12

相关论文

共 39 条

[1]

ASADA S, 1985, MAKROMOL CHEM, V186, P1755

[2] CONTINOUOUS SYNTHESIS OF OPTICALLY ACTIVE ALPHA-HYDROXYNITRILES [J].

BECKER, W ;

PFEIL, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (18) :4299-&

[3] STEREOSPECIFIC SYNTHESIS OF D-HYDROXYNITRILES AND OPTICALLY ACTIVE ETHANOLAMINES [J].

BECKER, W ;

FREUND, H ;

PFEIL, E .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1965, 4 (12) :1079-&

[4] BIO-ORGANIC SYNTHESIS OF OPTICALLY-ACTIVE CYANOHYDRINS AND ACYLOINS [J].

BRUSSEE, J ;

ROOS, EC ;

VANDERGEN, A .

TETRAHEDRON LETTERS, 1988, 29 (35) :4485-4488

[5] NMR MEASUREMENTS AND SEMIEMPIRICAL CALCULATIONS IN A 1ST APPROACH TO ELUCIDATE THE MECHANISM OF ENANTIOSELECTIVE CYANOHYDRIN FORMATION CATALYZED BY CYCLO-(S)-PHE-(S)-HIS [J].

CALLANT, D ;

COUSSENS, B ;

VANDERMATEN, T ;

DEVRIES, JG ;

DEVRIES, NK .

TETRAHEDRON-ASYMMETRY, 1992, 3 (03) :401-414

[6] ASYMMETRIC HYDROCYANATION OF BENZALDEHYDES CATALYZED BY (5R)-5-(4-IMIDAZOLYLMETHYL)-2,4-IMIDAZOLIDINEDIONE [J].

DANDA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (12) :3743-3745

[7] ASYMMETRIC HYDROCYANATION OF 3-PHENOXYBENZALDEHYDE CATALYZED BY POLY(CINCHONA ALKALOID-CO-ACRYLONITRILE)S [J].

DANDA, H ;

CHINO, K ;

WAKE, S .

CHEMISTRY LETTERS, 1991, (04) :731-732

[8]

DANDA H, 1991, SYNLETT, P263

[9] ENANTIOSELECTIVE AUTOINDUCTION IN THE ASYMMETRIC HYDROCYANATION OF 3-PHENOXYBENZALDEHYDE CATALYZED BY CYCLO[(R)-PHENYLALANYL-(R)-HISTIDYL] [J].

DANDA, H ;

NISHIKAWA, H ;

OTAKA, K .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6740-6741

[10] CONFORMATIONS OF PEPTIDES IN SOLUTION BY NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY .3. CYCLIC DIPEPTIDE RING CONFORMATIONS [J].

DAVIES, DB ;

KHALED, MA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (11) :1238-1244

← 1 2 3 4 →