Facile asymmetric synthesis of α-amino acids employing chiral ligand-mediated asymmetric addition reactions of phenyllithium with imines

被引：53

作者：

Hasegawa, M ^{[1
]}

Taniyama, D ^{[1
]}

Tomioka, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 52期

基金：

日本学术振兴会;

关键词：

alkylation; asymmetric synthesis; oxidation; amino acid;

D O I：

10.1016/S0040-4020(00)00860-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-step methodology involving an external chiral ligand-mediated asymmetric addition of phenyllithium to an anisidine imine, oxidative removal of N-PMP group, and finally oxidative conversion of the phenyl group to a carboxyl group provides a facile synthesis of optically pure alpha -amino acid derivatives bearing a bulky alpha -substituent. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：10153 / 10158

页数：6

共 61 条

[1] SURPRISING REACTIVITY OF (METHYL 2-ACETAMIDOACRYLATE)TRICARBONYLIRON(0) LEADING TO THE SYNTHESIS OF BETA,BETA,BETA-TRIALKYL ALPHA-AMINO-ACIDS [J].

BARKER, J ;

COOK, SL ;

LASTERRASANCHEZ, ME ;

THOMAS, SE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (11) :830-832

[2]

Beller M, 1998, CHEM-EUR J, V4, P935, DOI 10.1002/(SICI)1521-3765(19980515)4:5<935::AID-CHEM935>3.0.CO

[3]

2-#

[4] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[5] Synthesis and use of enantiomerically pure tert-leucine [J].

Bommarius, AS ;

Schwarm, M ;

Stingl, K ;

Kottenhahn, M ;

Huthmacher, K ;

Drauz, K .

TETRAHEDRON-ASYMMETRY, 1995, 6 (12) :2851-2888

[6] Stereoselective conjugate addition of organocuprates to a dehydroalanine derived diketopiperazine [J].

Bull, SD ;

Davies, SG ;

O'Shea, MD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (22) :3657-3658

[7] (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in the enantioselective preparation of α-amino acids [J].

Camps, P ;

Pérez, F ;

Soldevilla, N ;

Borrego, MA .

TETRAHEDRON-ASYMMETRY, 1999, 10 (03) :493-509

[8] Asymmetric 1,4 addition of Grignard reagents to chiral α,β-unsaturated esters in the presence of Lewis acids [J].

Cardillo, G ;

Gentilucci, L ;

Tolomelli, A ;

Tomasini, C .

TETRAHEDRON, 1999, 55 (19) :6231-6242

[9] Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds [J].

Cativiela, C ;

Diaz-de-Villegas, MD .

TETRAHEDRON-ASYMMETRY, 1998, 9 (20) :3517-3599

[10]

Chinchilla R, 1999, SYNTHESIS-STUTTGART, P704

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