New enantiodivergent procedure for the syntheses of chiral α-substituted serines from α-alkyl-α-aminomalonates utilizing enzymatic hydrolysis

被引：33

作者：

Sano, S ^{[1
]}

Hayashi, K ^{[1
]}

Miwa, T ^{[1
]}

Ishii, T ^{[1
]}

Fujii, M ^{[1
]}

Mima, H ^{[1
]}

Nagao, Y ^{[1
]}

机构：

[1] Univ Tokushima, Fac Pharmaceut Sci, Tokushima 7708505, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 31期

关键词：

amino acids and derivatives; asymmetric synthesis; enzymes and enzyme reactions; reduction;

D O I：

10.1016/S0040-4039(98)01123-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Porcine liver eaterase (PLE)- or rabbit liver eaterase (RLE)-catalyzed hydrolysis of the pro-S eater group of diethyl alpha-alkyl-alpha -(benzyloxycarbonylamino)malonate s 2a-e afforded (R)-ethyl alpha-alkyl-alpha -(benzyloxycarbonylamino)malonates 3a-e each in excellent enantiomeric excess. Enantiodivergent reductions of these acid eaters 3a-e readily furnished both the corresponding enantiomeric alpha-substituted serines (R)- and (S)-5a-c. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5571 / 5574

页数：4

共 13 条

[1] Pig liver esterase catalyzed hydrolysis of dimethyl and diethyl 2-methyl-2-(o-nitrophenoxy)malonates [J].

Breznik, M ;

Kikelj, D .

TETRAHEDRON-ASYMMETRY, 1997, 8 (03) :425-434

[2] ASYMMETRIC CONSTRUCTION OF QUATERNARY CARBONS FROM CHIRAL MALONATES - SELECTIVE AND VERSATILE TOTAL SYNTHESES OF THE ENANTIOMERS OF ALPHA-CUPARENONE AND BETA-CUPARENONE FROM A COMMON OPTICALLY-ACTIVE PRECURSOR [J].

CANET, JL ;

FADEL, A ;

SALAUN, J .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3463-3473

[3] Asymmetric construction of benzylic quaternary carbons from chiral malonates: Formal synthesis of both (-)- and (+)-aminoglutethimides AG and analogues [J].

Fadel, A ;

GarciaArgote, S .

TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :1159-1166

[4] FUNGAL METABOLITES .11. A POTENT IMMUNOSUPPRESSIVE ACTIVITY FOUND IN ISARIA-SINCLAIRII METABOLITE [J].

FUJITA, T ;

INOUE, K ;

YAMAMOTO, S ;

IKUMOTO, T ;

SASAKI, S ;

TOYAMA, R ;

CHIBA, K ;

HOSHINO, Y ;

OKUMOTO, T .

JOURNAL OF ANTIBIOTICS, 1994, 47 (02) :208-215

[5] FUNGAL METABOLITES .12. POTENT IMMUNOSUPPRESSANT, 14-DEOXOMYRIOCIN, (2S,3R,4R)-(E)-2-AMINO-3,4-DIHYDROXY-2-HYDROXYMETHYLEICOS-6-ENOIC ACID AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF MYRIOCIN DERIVATIVES [J].

FUJITA, T ;

INOUE, K ;

YAMAMOTO, S ;

IKUMOTO, T ;

SASAKI, S ;

TOYAMA, R ;

YONETA, M ;

CHIBA, K ;

HOSHINO, Y ;

OKUMOTO, T .

JOURNAL OF ANTIBIOTICS, 1994, 47 (02) :216-224

[6] IMPROVEMENT OF EFFICACY OF ANTITUMOR AGENTS BY CONAGENIN [J].

KAWATSU, M ;

YAMASHITA, T ;

ISHIZUKA, M ;

TAKEUCHI, T .

JOURNAL OF ANTIBIOTICS, 1995, 48 (03) :222-225

[7] Selective one-pot conversion of carboxylic acids into alcohols [J].

Kokotos, G ;

Noula, C .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :6994-6996

[8] EFFICIENT SYNTHESES OF THE 4 ENANTIOMERS AND DIASTEREOMERS OF ALPHA-METHYLTHREONINE AND BOTH ENANTIOMERS OF ALPHA-METHYLSERINE [J].

MOON, SH ;

OHFUNE, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7405-7406

[9] LACTACYSTIN, A NOVEL MICROBIAL METABOLITE, INDUCES NEURITOGENESIS OF NEUROBLASTOMA-CELLS [J].

OMURA, S ;

FUJIMOTO, T ;

OTOGURO, K ;

MATSUZAKI, K ;

MORIGUCHI, R ;

TANAKA, H ;

SASAKI, Y .

JOURNAL OF ANTIBIOTICS, 1991, 44 (01) :113-116

[10] LEWIS-ACID-MEDIATED AND CATIONIC LITHIUM-MEDIATED DIASTEREOSELECTIVE ALDOL-TYPE REACTION-BASED ON A DOUBLE CHIRAL RECOGNITION MANNER FOR THE ASYMMETRIC-SYNTHESIS OF ALPHA-SUBSTITUTED SERINES [J].

SANO, S ;

LIU, XK ;

TAKEBAYASHI, M ;

KOBAYASHI, Y ;

TABATA, K ;

SHIRO, M ;

NAGAO, Y .

TETRAHEDRON LETTERS, 1995, 36 (23) :4101-4104

← 1 2 →