STEREOSELECTIVE SYNTHESIS OF PROTECTED AMINES AND DIAMINES FROM ALKENES USING N,N-DICHLORO-TERT-BUTYLCARBAMATE

被引：39

作者：

ORLEK, BS ^{[1
]}

STEMP, G ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,MED RES CTR,COLDHARBOUR RD,HARLOW CM19 5AD,ESSEX,ENGLAND

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 32期

关键词：

CYCLIC ALKENES; AZIRIDINES; VICINAL DIAMINES; BOC-AMINES; N; N-DICHLORO-T-BUTYLCARBAMATE;

D O I：

10.1016/0040-4039(91)80624-F

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N,N-Dichloro-t-butylcarbamate (1) reacts with alkenes (2) in a regio- and stereo-selective manner to give the trans-chlorocarbamate adducts (3). Treatment of (3) with base gives aziridines (5), and reaction of (3) and (5) with sodium azide leads selectively to the versatile diamine precursors (6) and (7). In situ reduction of (3) with Zn/NH4OAc leads directly to Boc-protected amines (10).

引用

页码：4045 / 4048

页数：4

共 16 条

[1]

BAYLEY H, 1978, TETRAHEDRON LETT, P3633

[2]

BEAUMONT D, 1981, PROG MED CHEM, V18, P46

[3] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[4] CHROMOUS CHLORIDE PROMOTED ADDITION OF N-HALOAMIDES TO OLEFINS .3. SCOPE AND LIMITATIONS FOR SYNTHESIS OF N-(2-HALOALKYL)AMIDES [J].

DRIGUEZ, H ;

PATON, JM ;

LESSARD, J .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (04) :700-719

[5] PSEUDO-HALOGENS .8. NEW SYNTHESIS OF AZIRIDINES AND OXAZOLIDONES [J].

FOGLIA, TA ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (01) :75-&

[6] PSEUDO-HALOGENS .8. SCOPE AND MECHANISM OF ADDITION OF N,N-DICHLOROURETHAN TO MONOOLEFINIC COMPOUNDS [J].

FOGLIA, TA ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (11) :3625-&

[7]

Ganellin C R, 1967, Adv Drug Res, V4, P163

[8] SYNTHESIS AND DOPAMINERGIC ACTIVITY OF A NEW OXYGEN ISOSTERE OF THE 2-AMINOTETRALINS - N,N-DIPROPYL-8-HYDROXY-3-CHROMANAMINE [J].

HORN, AS ;

KAPTEIN, B ;

VERMUE, NA ;

DEVRIES, JB ;

MULDER, TBA .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1988, 23 (04) :325-328

[9] CONVERSION OF ALKYL CARBAMATES INTO AMINES VIA TREATMENT WITH TRIMETHYLSILYL IODIDE [J].

JUNG, ME ;

LYSTER, MA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (07) :315-316

[10]

Michalson E T, 1989, Prog Drug Res, V33, P135

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