DIASTEREOSELECTIVE ELECTROPHILIC AMINATION OF KETONE ENOLATES IN 2-SUBSTITUTED 2-ACYL-1,3-DITHIANE 1-OXIDES

被引：18

作者：

PAGE, PCB ^{[1
]}

ALLIN, SM ^{[1
]}

COLLINGTON, EW ^{[1
]}

CARR, RAE ^{[1
]}

机构：

[1] GLAXO GRP RES LTD,GREENFORD UB6 0HE,MIDDX,ENGLAND

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 15期

关键词：

D O I：

10.1016/0040-4039(94)85237-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enolate anions derived from 2-substituted 2-acyl-1,3-dithiane 1-oxides react readily with the nitrogen electrophile di-tert-butyl azodicarboxylate (DBAD) to give alpha-aminoketones with good diastereoselectivity and in reasonable yields; in some cases diastereoselectivity appears sufficiently high that the minor isomer cannot be detected by 400 MHz H-1 NMR spectroscopy.

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页码：2427 / 2430

页数：4

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共 21 条

[1] On derivatives of cyclo triazbutane [J].

Diels, O ;

Behncke, H .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1924, 57 :653-656

[2] STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-HYDRAZINO AND ALPHA-AMINO-ACID DERIVATIVES [J].

EVANS, DA ;

BRITTON, TC ;

DOROW, RL ;

DELLARIA, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6395-6397

[3] A GENERAL-APPROACH TO THE ASYMMETRIC-SYNTHESIS OF VANCOMYCIN-RELATED ARYLGLYCINES BY ENOLATE AZIDATION [J].

EVANS, DA ;

EVRARD, DA ;

RYCHNOVSKY, SD ;

FRUH, T ;

WHITTINGHAM, WG ;

DEVRIES, KM .

TETRAHEDRON LETTERS, 1992, 33 (09) :1189-1192

[4] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030

[5] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO AND ALPHA-HYDRAZINO ACID-DERIVATIVES VIA THE STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES WITH AZODICARBOXYLATE ESTERS [J].

EVANS, DA ;

BRITTON, TC ;

DOROW, RL ;

DELLARIA, JF .

TETRAHEDRON, 1988, 44 (17) :5525-5540

[6] REDUCTIVE CLEAVAGE OF THE NITROGEN NITROGEN BOND IN HYDRAZINE DERIVATIVES [J].

MELLOR, JM ;

SMITH, NM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (12) :2927-2931

[7] ENANTIOSELECTIVE SYNTHESES OF ALPHA-AMINO-ACIDS FROM 10-(AMINOSULFONYL)-2-BORNYL ESTERS AND DI(TERT-BUTYL) AZODICARBOXYLATE [J].

OPPOLZER, W ;

MORETTI, R .

HELVETICA CHIMICA ACTA, 1986, 69 (08) :1923-1926

[8] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS AND ALPHA-N-HYDROXYAMINO ACIDS VIA ELECTROPHILIC AMINATION OF BORNANESULTAM-DERIVED ENOLATES WITH 1-CHLORO-1-NITROSOCYCLOHEXANE [J].

OPPOLZER, W ;

TAMURA, O .

TETRAHEDRON LETTERS, 1990, 31 (07) :991-994

[9] HIGH DIASTEREOFACIAL SELECTIVITY IN ASYMMETRIC MANNICH REACTION OF ACYLDITHIANE OXIDE ENOLATES [J].

PAGE, PCB ;

ALLIN, SM ;

COLLINGTON, EW ;

CARR, RAE .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6902-6904

[10] DIASTEREOSELECTIVE ALKYLATION OF KETONE ENOLATES USING A 1,3-DITHIANE 1-OXIDE AUXILIARY [J].

PAGE, PCB ;

SLAWIN, AMZ ;

WESTWOOD, D ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01) :185-187