Facile synthesis of 3-hydroxyglutamic acids via cyanation of chiral N-acyliminium cation derived from (S)-malic acid

被引：10

作者：

Oba, M ^{[1
]}

Mita, A ^{[1
]}

Kondo, Y ^{[1
]}

Nishiyama, K ^{[1
]}

机构：

[1] Tokai Univ, Dept Chem Mat, Shizuoka 4100395, Japan

来源：

SYNTHETIC COMMUNICATIONS | 2005年 / 35卷 / 23期

关键词：

cyanation; 3-hydroxyglutamic acid; malic acid; N-acyliminium cation;

D O I：

10.1080/00397910500278446

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Facile synthesis of 3-hydroxyglutamic acids via cyanation of an N- acyliminium intermediate derived from (S)-malic acid is described. The chiral cyclic imide derived from (S)-malic acid was converted to an acetoxylactam by reduction with sodium borohydride followed by acetylation. The obtained acetoxylactam was treated with trimethylsilyl cyanide in the presence of boron trifluoride etherate to give the corresponding cyanolactam in high yield, even though the diastereoselectivity of the cyanation reaction was moderate. The diastereomers of the cyanolactam were chromatographically separable and were independently converted to (2R,3S)- and (2S,3S)-3-hydroxyglutamic acids.

引用

页码：2961 / 2966

页数：6

共 45 条

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