Enantiomerically enriched (R)- and (S)-α-methylphenylalanine via asymmetric PTC C-alkylation catalysed by NOBIN

被引：69

作者：

Belokon', YN

Kochetkov, KA

Churkina, TD

Ikonnikov, NS

Vyskocil, S

Kagan, HB

机构：

[1] Russian Acad Sci, Inst Organoelement Cpds, Moscow 117813, Russia

[2] Charles Univ, Fac Sci, Dept Organ Chem, Prague 12840 2, Czech Republic

[3] Inst Chim Mol Orsay, Lab Synthese Asymetr, CNRS, Paris, France

[4] Univ Paris Sud, F-91405 Orsay, France

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(99)00185-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiopure 2-hydroxy-2'-amino-1,1'-binaphthyl (NOBIN) is shown to catalyse C-alkylation of aldimine Schiff's bases of alanine ester under phase-transfer catalysis conditions (solid NaOH or NaH, toluene, ambient temperature, 10% NOBIN). Using (R)-NOBIN, the final (S)-alpha-methylphenylalanine was obtained in up to 68% ee. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

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页码：1723 / 1728

页数：6

相关论文

共 38 条

[1] The role of monomer in alkylation reactions of the lithium enolate of p-phenylisobutyrophenone in tetrahydrofuran [J].

Abbotto, A ;

Leung, SSW ;

Streitwieser, A ;

Kilway, KV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) :10807-10813

[2] Enantiospecific alkylations of alanine [J].

Alonso, F ;

Davies, SG ;

Elend, AS ;

Haggitt, JL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (02) :257-264

[3] Asymmetric synthesis of α,β-epoxysulfones under phase-transfer catalyzed Darzens reaction [J].

Arai, S ;

Ishida, T ;

Shioiri, T .

TETRAHEDRON LETTERS, 1998, 39 (45) :8299-8302

[4] Catalytic asymmetric Darzens condensation under phase-transfer-catalyzed conditions [J].

Arai, S ;

Shioiri, T .

TETRAHEDRON LETTERS, 1998, 39 (15) :2145-2148

[5]

Belokon YN, 1997, MENDELEEV COMMUN, P137

[6] GENERAL-METHOD FOR THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS VIA ALKYLATION OF THE CHIRAL NICKEL(II) SCHIFF-BASE COMPLEXES OF GLYCINE AND ALANINE [J].

BELOKON, YN ;

BAKHMUTOV, VI ;

CHERNOGLAZOVA, NI ;

KOCHETKOV, KA ;

VITT, SV ;

GARBALINSKAYA, NS ;

BELIKOV, VM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (02) :305-312

[7] Asymmetric PTC C-alkylation mediated by TADDOL -: novel route to enantiomerically enriched α-alkyl-α-amino acids [J].

Belokon, YN ;

Kochetkov, KA ;

Churkina, TD ;

Ikonnikov, NS ;

Chesnokov, AA ;

Larionov, OV ;

Parmár, VS ;

Kumar, R ;

Kagan, HB .

TETRAHEDRON-ASYMMETRY, 1998, 9 (05) :851-857

[8]

BELOKON YN, 1999, B RUS ACAD SCI DIV C, V48, P917

[9]

BELOKON YN, 1998, B ACAD SCI DIV CHEM, V47, P74

[10] ACIDITIES OF ANILINES IN DIMETHYL-SULFOXIDE SOLUTION [J].

BORDWELL, FG ;

ALGRIM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (09) :2964-2968

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