(S)-α-methyl,α-amino acids: a new stereocontrolled synthesis

被引：8

作者：

Balducci, Daniele ^{[1
]}

Lazzari, Ilaria ^{[2
]}

Monari, Magda ^{[1
]}

Piccinelli, Fabio ^{[3
]}

Porzi, Gianni ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

[2] Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy

[3] Univ Verona, Lab Chim Stato Solido DB, I-37100 Verona, Italy

来源：

AMINO ACIDS | 2010年 / 38卷 / 03期

关键词：

Diketopiperazine derivatives; alpha-Methyl-alpha-amino acids; Asymmetric synthesis; ALPHA-AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE ALKYLATION; ENANTIOSELECTIVE SYNTHESIS; PART; DERIVATIVES; ANALOGS;

D O I：

10.1007/s00726-009-0289-9

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A new and convenient stereocontrolled synthesis of the optically pure (S)-alpha-methyl,alpha-amino acids 6(a-d) that exploits the chiral synthon 1,4-N,N-[(S)-1-phenylethyl]-piperazine-2,5-dione (1) is described. The (S)-1-phenylethyl group, bonded to each of the N-atoms of the 2,5-diketopiperazine, acts as a chiral inductor in the first alkylation, while the steric hindrance appears to be the determining factor of stereocontrol in third and forth alkylation.

引用

页码：829 / 837

页数：9

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