STEREOSPECIFIC SYNTHESIS OF ALPHA-DEUTERIATED ALPHA-AMINO-ACIDS - REGIOSPECIFIC DEUTERIATION OF CHIRAL 3-ISOPROPYL-2,5-DIMETHOXY-3,6-DIHYDROPYRAZINES

被引：42

作者：

ROSE, JE

LEESON, PD

GANI, D

机构：

[1] UNIV ST ANDREWS,DEPT CHEM,ST ANDREWS KY16 9ST,FIFE,SCOTLAND

[2] MERCK SHARP & DOHME LTD,NEUROSCI RES CTR,HARLOW CM20 2QR,ESSEX,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 02期

关键词：

D O I：

10.1039/p19950000157

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Base-catalysed deuteriation of (3R)- or (3S)-3-isopropyl-2.5-dimethoxy-3,6-dihydropyrazines in refluxing (CH3OH)-H-2-(H2O)-H-2 gives the [6-H-2(2)]-isotopomer in excellent yields without disturbing the stereogenic centre at C-3. These compounds provide convenient and efficient access to a range of (R)- and (S)-alpha-deuteriated alpha-amino acids, including serine, aspartic acid, allylglycine and phenylalanine, via alkylation of the butyllithium generated C-6 anion.

引用

页码：157 / 165

页数：9

共 21 条

[1]

ARCHER CA, 1994, TETRAHEDRON-ASYMMETR, V4, P1141

[2]

BLACK S, 1955, J BIOL CHEM, V213, P39

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