alpha-aryl O-vinyl carbamates. Tandem carbolithiation-alpha-alkylation and -[1,2]-Wittig rearrangement reactions

被引：24

作者：

Superchi, S ^{[1
]}

Sotomayor, N ^{[1
]}

Miao, GB ^{[1
]}

Joseph, B ^{[1
]}

Campbell, MG ^{[1
]}

Snieckus, V ^{[1
]}

机构：

[1] UNIV WATERLOO,GUELPH WATERLOO CTR GRAD WORK CHEM,WATERLOO,ON N2L 3G1,CANADA

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 34期

关键词：

D O I：

10.1016/0040-4039(96)01315-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient, one-pot carbolithiation - alpha-alkylation and -[1.2]-Wittig rearrangement processes of alpha-aryl O-vinyl carbamates 1 to branched benzyl O-carbamates 3 and 2-aryl-2-hydroxypropionamides 4, including Naproxen analogues, is described. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：6061 / 6064

页数：4

共 18 条

[1]

BAILEY WF, 1994, FMC LITHIUM LINK SPR, P8

[2] STEREOCONTROL AND REGIOCONTROL BY COMPLEX INDUCED PROXIMITY EFFECTS - REACTIONS OF ORGANOLITHIUM COMPOUNDS [J].

BEAK, P ;

MEYERS, AI .

ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (11) :356-363

[3] ORGANOALKALI COMPOUNDS BY RADICAL-ANION INDUCED REDUCTIVE METALATION OF PHENYL THIOETHERS [J].

COHEN, T ;

BHUPATHY, M .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (04) :152-161

[4]

EMBER L, 1994, C EN NEWS 0815, P5

[5]

Haggin J., 1994, CHEM ENG NEWS 0704, P23

[6] A NOVEL ENTRY INTO WITTIG REARRANGEMENTS - A STEREOSELECTIVE [1,2]-WITTIG REARRANGEMENT WITH INVERSION OF CONFIGURATION AT THE CARBANION CENTER [J].

HOFFMANN, R ;

BRUCKNER, R .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (08) :1957-1963

[7] METALATED NITROGEN DERIVATIVES OF CARBONIC-ACID IN ORGANIC-SYNTHESIS .28. THE HOMOALDOL REACTION, OR HOW TO OVERCOME PROBLEMS OF REGIO-SELECTIVITY AND STEREO-SELECTIVITY [J].

HOPPE, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (12) :932-948

[8]

KATO T, 1990, SYNLETT, P671

[9] BENZOTRIAZOLE-ASSISTED BETA-LITHIATION OF VINYL ETHERS [J].

KATRITZKY, AR ;

IGNATCHENKO, AV ;

LAN, XF ;

LANG, HY ;

STEVENS, CV ;

OPITZ, A ;

KOCH, R ;

ANDERS, E .

TETRAHEDRON, 1994, 50 (20) :6005-6016

[10] ASYMMETRIC CARBOLITHIATION OF CINNAMYL DERIVATIVES IN THE PRESENCE OF (-)-SPARTEINE [J].

KLEIN, S ;

MAREK, I ;

POISSON, JF ;

NORMANT, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (34) :8853-8854

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