Asymmetric Synthesis of the Nonproteinogenic Silicon-Containing α-Amino Acids (R)- and (S)-α-[(Trimethylsilyl)methyl]alanine

被引：11

作者：

Falgner, Steffen ^{[1
]}

Burschka, Christian ^{[1
]}

Wagner, Stephan ^{[1
]}

Boehm, Andreas ^{[2
]}

Daiss, Juergen O. ^{[2
]}

Tacke, Reinhold ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Anorgan Chem, D-97074 Wurzburg, Germany

[2] Corp R&D, Wacker Chem AG, D-81379 Munich, Germany

来源：

ORGANOMETALLICS | 2009年 / 28卷 / 20期

关键词：

ABSOLUTE-STRUCTURE; SILAPROLINE; STRATEGIES; PEPTIDES; PROLINE; SI;

D O I：

10.1021/om900583d

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The nonproteinogenic silicon-containing, alpha,alpha-disubstituted alpha-amino acids (R)- and (S)-2-amino-2-methyl-3-(trimethylsilyl)propanoic acid [(R)- and (S)-alpha-[(trimethylsilyl)methyl]alanine, (R)-1 and (S)-1] were synthesized by multistep syntheses, starting from diethyl malonate, and both were isolated with an enantiomeric purity of > 99% ee. Compound rac-1 was also prepared. The key step of the asymmetric syntheses of (R)-1 and (S)-1 was all enantioselective enzyme-catalyzed (porcine liver esterase) ester cleavage of the prochiral substrate diethyl methyl[(trimethylsilyl)methyl]malonate. The absolute configurations of (R)-1 and (S)-1 were established by crystal structure analyses of (R)-1 and of its rhodium complex (S-Rh,R-C)-16.

引用

页码：6059 / 6066

页数：8

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