Regio- and stereoselective ring opening reaction of 2,3-epoxy amines with organo-aluminum reagents leading to 2-substituted 3-amino alcohols

被引：10

作者：

Liu, CQ ^{[1
]}

Hashimoto, Y ^{[1
]}

Saigo, K ^{[1
]}

机构：

[1] UNIV TOKYO,GRAD SCH ENGN,DEPT CHEM & BIOTECHNOL,BUNKYO KU,TOKYO 113,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 34期

关键词：

D O I：

10.1016/0040-4039(96)01341-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylation, alkynylation, and hydride reduction occurred regioselectively at the C-2 position of 2,3-epoxy amines with retention of the configuration at the C-2 upon treatment with organoaluminum reagents to give 2-substituted 3-amino alcohols. The reactions are considered to proceed via aziridinium ion intermediates. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：6177 / 6180

页数：4

共 16 条

[1]

Behrens C. H., 1983, ALDRICHIM ACTA, V16, P67

[2]

Finn M. G., 1985, ASYMMETRIC SYNTHESIS, V5, P247

[3]

GILL GM, 1996, TETRAHEDRON, V52, P3609

[4]

Glasby J., 1979, ENCY ANTIBIOTICS

[5] THE SYNTHETIC METHODOLOGY OF NONRACEMIC GLYCIDOL AND RELATED 2,3-EPOXY ALCOHOLS [J].

HANSON, RM .

CHEMICAL REVIEWS, 1991, 91 (04) :437-475

[6]

Johnson R.A, 1991, Comp. Org. Synth, V7, P389

[7] THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].

KATSUKI, T ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976

[8]

LIU C, 1996, IN PRESS B CHEM SOC, V69

[9] LEWIS-ACID INDUCED REARRANGEMENT OF 2,3-EPOXY AMINES - CHARACTERIZATION OF AZIRIDINIUM ION INTERMEDIATES AND REGIOSPECIFIC RING-OPENING WITH NITROGEN NUCLEOPHILES [J].

LIU, QY ;

SIMMS, MJ ;

BODEN, N ;

RAYNER, CM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (11) :1363-1365

[10]

LIU QY, 1995, SYNLETT, P1037

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