1H NMR study of the hydrolysis of N-acylhydroxy[2H]methylpyrroles

被引：10

作者：

Abell, AD ^{[1
]}

Litten, JC ^{[1
]}

Nabbs, BK ^{[1
]}

机构：

[1] Univ Canterbury, Dept Chem, Christchurch 1, New Zealand

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 08期

关键词：

D O I：

10.1039/a801276h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

KOH catalysed hydrolysis of the (S)- and (R)-N-(N-phthalylleucinyl)hydroxy[H-2]methylpyrroles 6b and 6c, in CD3CN containing 1 equiv. of (+)-sec-butylamine, proceeds by an initial N- to O-acyl transfer with retention of configuration at the labelled centre, followed by trapping of an azafulvene to give (S)- and (R)-sec-butylamino[H-2]methylpyrroles 9b.

引用

页码：919 / 920

页数：2

共 11 条

[1] SYNTHESIS AND HYDROLYSIS OF DIPEPTIDE ISOSTERES CONTAINING A PROLINE ANALOG WITH LATENT REACTIVITY [J].

ABELL, AD ;

LITTEN, JC .

TETRAHEDRON LETTERS, 1992, 33 (21) :3005-3008

[2] SYNTHESIS AND AMINO-ACID CHAIN EXTENSION OF 1-ACYLATED HYDROXYMETHYLPYRROLES [J].

ABELL, AD ;

LITTEN, JC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1993, 46 (10) :1473-1483

[3] Synthesis and properties of ring-deactivated deuterated (hydroxymethyl)pyrroles [J].

Abell, AD ;

Nabbs, BK ;

Battersby, AR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1741-1746

[4]

[Anonymous], 1984, COMPREHENSIVE HETERO

[5] 1-AZAFULVENES AND 2-AZAFULVENES [J].

BARCOCK, RA ;

MOORCROFT, NA ;

STORR, RC ;

YOUNG, JH ;

FULLER, LS .

TETRAHEDRON LETTERS, 1993, 34 (07) :1187-1190

[6]

BATTERSBY AR, 1982, J CHEM SOC PERK T 1, P2427, DOI 10.1039/p19820002427

[7]

Jones A, 1977, CHEM PYRROLES

[8]

ORTEGA MJ, 1997, TETRAHEDRON LETT, V38, P331

[9]

SAVRDA J, 1992, TETRAHEDRON, V33, P3005

[10] STEREOCHEMISTRY OF FORMATION OF THE HYDROXYMETHYL GROUP OF HYDROXYMETHYLBILANE, THE PRECURSOR OF UROGEN-III [J].

SCHAUDER, JR ;

JENDREZEJEWSKI, S ;

ABELL, A ;

HART, GJ ;

BATTERSBY, AR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (06) :436-438

← 1 2 →