Asymmetric synthesis of α-amino acids:: indium-mediated reactions of glyoxylic oxime ether in aqueous media

被引：74

作者：

Miyabe, H ^{[1
]}

Nishimura, A ^{[1
]}

Ueda, M ^{[1
]}

Naito, T ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Kobe, Hyogo 6588558, Japan

来源：

CHEMICAL COMMUNICATIONS | 2002年 / 14期

关键词：

D O I：

10.1039/b203493j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The indium-mediated allylation and alkylation reactions of the Oppolzer camphorsultam derivative of glyoxylic oxime ether proceeded with excellent diastereoselectivity in aqueous media, providing a variety of enantiomerically pure a amino acids.

引用

页码：1454 / 1455

页数：2

共 29 条

[1] ENANTIOSELECTIVE SYNTHESIS OF HOMOALLYLIC AMINES BY ADDITION OF ALLYLMETAL REAGENTS TO IMINES DERIVED FROM (S)-VALINE ESTERS [J].

BASILE, T ;

BOCOUM, A ;

SAVOIA, D ;

UMANIRONCHI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7766-7773

[2] INDIUM-MEDIATED ALLYLATION OF ALDIMINES [J].

BEUCHET, P ;

LEMARREC, N ;

MOSSET, P .

TETRAHEDRON LETTERS, 1992, 33 (40) :5959-5960

[3] Organometallic reactions in aqueous media. Indium-mediated allylation of sulfonimines [J].

Chan, TH ;

Lu, WS .

TETRAHEDRON LETTERS, 1998, 39 (47) :8605-8608

[4] Indium-mediated organometallic reactions in aqueous media: The nature of the allylindium intermediate [J].

Chan, TH ;

Yang, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3228-3229

[5] Use of α-chlorosulfides in indium promoted C-C couplings:: easy entry into the stereoselective formation of epoxy alkynes [J].

Engstrom, G ;

Morelli, M ;

Palomo, C ;

Mitzel, T .

TETRAHEDRON LETTERS, 1999, 40 (33) :5967-5970

[6] 1,5-ASYMMETRIC INDUCTION IN REACTIONS BETWEEN 4-ALKOXY-PENT-2-ENYL(TRIBUTYL)STANNANES AND 5-ALKOXY-PENT-2-ENYL(TRIBUTYL)STANNANES AND ACHIRAL 1-ALKOXYCARIBONYLIMINES [J].

HALLETT, DJ ;

THOMAS, EJ .

TETRAHEDRON-ASYMMETRY, 1995, 6 (10) :2575-2578

[7] REMOTE ASYMMETRIC INDUCTION IN REACTIONS BETWEEN 4-BENZYLOXYPENT-2-ENYL(TRIBUTYL)STANNANE AND 5-BENZYLOXYPENT-2-ENYL(TRIBUTYL)STANNANE AND CHIRAL IMINES PREPARED FROM BUTYL GLYOXYLATE [J].

HALLETT, DJ ;

THOMAS, EJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (06) :657-658

[8] Asymmetric synthesis of L-azetidine-2-carboxylic acid and 3-substituted congeners - Conformationally constrained analogs of phenylalanine, naphthylalanine, and leucine [J].

Hanessian, S ;

Bernstein, N ;

Yang, RY ;

Maguire, R .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (10) :1437-1442

[9]

Hanessian S, 1999, ANGEW CHEM INT EDIT, V38, P3160

[10] The asymmetric synthesis of allylglycine and other unnatural alpha-amino acids via zinc-mediated allylation of oximes in aqueous media [J].

Hanessian, S ;

Yang, RY .

TETRAHEDRON LETTERS, 1996, 37 (30) :5273-5276

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