ENANTIOSELECTIVE SYNTHESIS OF ALPHA-BRANCHED ALPHA-AMINO-ACIDS WITH BULKY SUBSTITUENTS

被引：0

作者：

STUDER, A ^{[1
]}

SEEBACH, D ^{[1
]}

机构：

[1] ETH ZURICH,ORGAN CHEM LAB,CH-8092 ZURICH,SWITZERLAND

来源：

LIEBIGS ANNALEN | 1995年 / 02期

关键词：

AMINO ACIDS; ALPHA-BRANCHED; HIGHLY HINDERED AMIDES; HYDROLYSIS OF AMINO ACID AMIDES; ANCHIMERIC EFFECT; PHENYLALANINE; 2-ETHYL-; 2-I-PROPYL-; AND; 2-CYCLOHEXYLMETHYL-;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiopure 5,5-disubstituted t-butyl 2-t-butyl-3-methyl-4-oxoimidazolidine-1-carboxylates readily available by diastereoselective double alkylation of the parent compound (Boc-BMI) can be converted to alpha-branched alpha-amino acids with two bulky substituents (PhCH(2)/Et, PhCH(2)/i-Pr, PhCH(2)/CH2C6H11) in four simple steps: hydrolysis to the amino acid amides, N-benzoylation, cleavage of the amino acid amide group, and debenzoylation (Scheme 3, products 6-10, overall yields >50%). This procedure constitutes an extension of the scope of amino acid synthesis from (R)- and (S)-Boc-BMI.

引用

页码：217 / 222

页数：6

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