Highly Enantioselective Synthesis of (S)-α-Alkyl-α,β-diaminopropionic Acids via Asymmetric Phase-Transfer Catalytic Alkylation of 2-Phenyl-2-imidazoline-4-carboxylic Acid tert-Butyl Esters

被引：32

作者：

Park, Yohan ^{[1
,2
]}

Kang, Sukhoon ^{[1
,2
]}

Lee, Young Ju ^{[1
,2
]}

Kim, Taek-Soo ^{[1
,2
]}

Jeong, Byeong-Seon ^{[3
]}

Park, Hyeung-geun ^{[1
,2
]}

Jew, Sang-sup ^{[1
,2
]}

机构：

[1] Seoul Natl Univ, Res Inst Pharmaceut Sci, Seoul 151742, South Korea

[2] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea

[3] Yeungnam Univ, Coll Pharm, Gyongsan 712749, South Korea

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 16期

关键词：

ALPHA-AMINO-ACIDS; STEREOSELECTIVE AMINATION; ALPHA; BETA-DIAMINO ACIDS; COMPLEX;

D O I：

10.1021/ol9013552

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient enantioselective synthetic method for (S)-alpha-alkyl-alpha,beta-diaminopropionic acid is reported. The asymmetric phase-transfer catalytic alkylation of N(1)-Boc-2-phenyl-2-imidazoline-4-carboxylic acid tert -butyl ester in the presence of chiral quaternary ammonium catalyst gave the corresponding alkylated products (93-98% ee) which could be transformed to enantioenriched alpha-alkyl-alpha,beta-diaminopropionic acids.

引用

页码：3738 / 3741

页数：4

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