Catalytic enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxybenzaldehyde using cyclo-His-(alpha-Me)Phe as catalyst

R Hulst; QB Broxterman; Johan Kamphuis; F Formaggio; M Crisma; C Toniolo; RM Kellogg

doi:10.1016/S0957-4166(97)00178-X

Catalytic enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxybenzaldehyde using cyclo-His-(alpha-Me)Phe as catalyst

R Hulst
, QB Broxterman^*
, Johan Kamphuis
, F Formaggio
, M Crisma
, C Toniolo
, RM Kellogg

^*Corresponding author for this work

Molecular Inorganic Chemistry

Research output: Contribution to journal › Article › Academic › peer-review

19 Citations (Scopus)

Abstract

Two cyclo-dipeptides based on His and the unnatural (alpha Me)Phe have been examined as catalysts in the enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxy-benzaldehyde. The synthesis, catalytic activity and NMR study towards the mechanism of this reaction are presented. (C) 1997 Elsevier Science Ltd.

Original language	English
Pages (from-to)	1987-1999
Number of pages	13
Journal	Tetrahedron-Asymmetry
Volume	8
Issue number	12
DOIs	https://doi.org/10.1016/S0957-4166(97)00178-X
Publication status	Published - 27-Jun-1997

Keywords

ENANTIOMERIC EXCESS DETERMINATION
STATE CONFORMATIONAL-ANALYSIS
SYNTHETIC CYCLIC PEPTIDE
UNPROTECTED AMINO-ACIDS
HELICAL SCREW SENSE
C-ALPHA-METHYL
ASYMMETRIC ADDITION
P-31 NMR
C-ALPHA,ALPHA-DISUBSTITUTED GLYCINES
STRUCTURAL VERSATILITY

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Catalytic enantioselective addition of hydrogen cyanide to benzaldehyde
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title = "Catalytic enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxybenzaldehyde using cyclo-His-(alpha-Me)Phe as catalyst",

abstract = "Two cyclo-dipeptides based on His and the unnatural (alpha Me)Phe have been examined as catalysts in the enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxy-benzaldehyde. The synthesis, catalytic activity and NMR study towards the mechanism of this reaction are presented. (C) 1997 Elsevier Science Ltd.",

keywords = "ENANTIOMERIC EXCESS DETERMINATION, STATE CONFORMATIONAL-ANALYSIS, SYNTHETIC CYCLIC PEPTIDE, UNPROTECTED AMINO-ACIDS, HELICAL SCREW SENSE, C-ALPHA-METHYL, ASYMMETRIC ADDITION, P-31 NMR, C-ALPHA,ALPHA-DISUBSTITUTED GLYCINES, STRUCTURAL VERSATILITY",

author = "R Hulst and QB Broxterman and Johan Kamphuis and F Formaggio and M Crisma and C Toniolo and RM Kellogg",

year = "1997",

month = jun,

day = "27",

doi = "10.1016/S0957-4166(97)00178-X",

language = "English",

volume = "8",

pages = "1987--1999",

journal = "Tetrahedron-Asymmetry",

issn = "0957-4166",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

number = "12",

}

TY - JOUR

T1 - Catalytic enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxybenzaldehyde using cyclo-His-(alpha-Me)Phe as catalyst

AU - Hulst, R

AU - Broxterman, QB

AU - Kamphuis, Johan

AU - Formaggio, F

AU - Crisma, M

AU - Toniolo, C

AU - Kellogg, RM

PY - 1997/6/27

Y1 - 1997/6/27

N2 - Two cyclo-dipeptides based on His and the unnatural (alpha Me)Phe have been examined as catalysts in the enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxy-benzaldehyde. The synthesis, catalytic activity and NMR study towards the mechanism of this reaction are presented. (C) 1997 Elsevier Science Ltd.

AB - Two cyclo-dipeptides based on His and the unnatural (alpha Me)Phe have been examined as catalysts in the enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxy-benzaldehyde. The synthesis, catalytic activity and NMR study towards the mechanism of this reaction are presented. (C) 1997 Elsevier Science Ltd.

KW - ENANTIOMERIC EXCESS DETERMINATION

KW - STATE CONFORMATIONAL-ANALYSIS

KW - SYNTHETIC CYCLIC PEPTIDE

KW - UNPROTECTED AMINO-ACIDS

KW - HELICAL SCREW SENSE

KW - C-ALPHA-METHYL

KW - ASYMMETRIC ADDITION

KW - P-31 NMR

KW - C-ALPHA,ALPHA-DISUBSTITUTED GLYCINES

KW - STRUCTURAL VERSATILITY

U2 - 10.1016/S0957-4166(97)00178-X

DO - 10.1016/S0957-4166(97)00178-X

M3 - Article

SN - 0957-4166

VL - 8

SP - 1987

EP - 1999

JO - Tetrahedron-Asymmetry

JF - Tetrahedron-Asymmetry

IS - 12

ER -

Catalytic enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxybenzaldehyde using cyclo-His-(alpha-Me)Phe as catalyst

Abstract

Keywords

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