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.
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页码：217 / 222
页数：6
相关论文
共 63 条
[1]   PRELIMINARY BIOLOGICAL STUDIES OF CERTAIN AMINO-ACID ANALOGS [J].
ABSHIRE, CJ ;
OSTIGUY, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (07) :965-966
[2]   OVERALL ENANTIOSELECTIVE ALPHA-ALKYLATION OF ASPARTIC AND GLUTAMIC-ACID THROUGH DILITHIUM ENOLATOCARBOXYLATES OF 2-[3-BENZOYL-2-(TERT-BUTYL)-1-METHYL-5-OXOIMIDAZOLIDIN-4-YL]ACETIC AND 3-[3-BENZOYL-2-(TERT-BUTYL)-1-METHYL-5-OXOIMIDAZOLIDIN-4-YL]PROPIONIC ACID, RESPECTIVELY [J].
AEBI, JD ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1985, 68 (06) :1507-1518
[3]   INTERACTION OF ALPHA-CHYMOTRYPSIN WITH SEVERAL ALPHA-METHYL-ALPHA-ACYLAMINO ACID METHYL ESTERS [J].
ALMOND, HR ;
MANNING, DT ;
NIEMANN, C .
BIOCHEMISTRY, 1962, 1 (02) :243-&
[4]   VERSATILE STEREOSELECTIVE SYNTHESIS OF COMPLETELY PROTECTED TRIFUNCTIONAL ALPHA-METHYLATED ALPHA-AMINO-ACIDS STARTING FROM ALANINE [J].
ALTMANN, E ;
NEBEL, K ;
MUTTER, M .
HELVETICA CHIMICA ACTA, 1991, 74 (04) :800-806
[5]   OPTICAL ENANTIOMORPHS OF ISOVALINE [J].
BAKER, CG ;
FU, SCJ ;
BIRNBAUM, SM ;
SOBER, HA ;
GREENSTEIN, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (18) :4701-4702
[6]   STEREOCHEMISTRY OF ALPHA-AMINOISOBUTYRIC-ACID PEPTIDES IN SOLUTION - CONFORMATIONS OF DECAPEPTIDES WITH A CENTRAL TRIPLET OF CONTIGUOUS L-AMINO-ACIDS [J].
BALARAM, H ;
SUKUMAR, M ;
BALARAM, P .
BIOPOLYMERS, 1986, 25 (11) :2209-2223
[7]   PREPARATION OF OPTICALLY PURE ALPHA-METHYL-ALPHA-AMINO ACIDS VIA ALKYLATION OF THE NICKEL(II) SCHIFF-BASE OF (R,S)-ALANINE WITH (S)-2-N-(N'-BENZYLPROLYL)AMINOBENZALDEHYDE [J].
BELOKON, YN ;
CHERNOGLAZOVA, NI ;
KOCHETKOV, CA ;
GARBALINSKAYA, NS ;
BELIKOV, VM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (03) :171-172
[8]  
BEY P, 1977, TETRAHEDRON LETT, P1455
[9]   RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
DUTHALER, RO .
TETRAHEDRON, 1994, 50 (06) :1539-1650
[10]  
Ehrlich F, 1908, BIOCHEM Z, V8, P438
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