Chelated [3,3]-rearrangements of difluoroallylic alcohols.

被引：16

作者：

Broadhurst, MJ

Percy, JM

Prime, ME

机构：

[1] UNIV BIRMINGHAM,SCH CHEM,BIRMINGHAM B15 2TT,W MIDLANDS,ENGLAND

[2] ROCHE DISCOVERY WELWYN,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 33期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(97)01315-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Whereas the lithium enolates of acetate and propionate esters of difluoroallylic alcohols fragment rapidly, even at -78 degrees C, methoxy-and benzyloxy-acetates form chelated enolates which undergo smooth [3,3]-rearrangement as their silyl ketene acetals. The latent ketone function can be revealed under mild conditions (MeOH, SOCl2) to afford very highly functionalised CF2 compounds. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：5903 / 5906

页数：4

相关论文

共 19 条

[1]

Andres JM, 1996, SYNTHESIS-STUTTGART, P1070

[2] Facile [2,3]-rearrangements of difluoroallylic alcohols with C-P and C-S bond formation [J].

Blades, K ;

Patel, ST ;

Percy, JM ;

Wilkes, RD .

TETRAHEDRON LETTERS, 1996, 37 (35) :6403-6406

[3]

BRAUN M, 1995, LIEBIGS ANN, P1447

[4] SYNTHESIS OF DIFLUOROENOXYSILANES FROM ACYLSILANES AND TRIFLUOROMETHYLTRIMETHYLSILANE (TFMTMS) - DRAMATIC EFFECT OF THE CATALYTIC FLUORIDE SOURCE [J].

BRIGAUD, T ;

DOUSSOT, P ;

PORTELLA, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) :2117-2118

[5] An efficient general method for esterification of aromatic carboxylic acids [J].

Hosangadi, BD ;

Dave, RH .

TETRAHEDRON LETTERS, 1996, 37 (35) :6375-6378

[6] THE ALDOL REACTION WITH DIFLUOROENOLATES [J].

HOWARTH, JA ;

OWTON, WM ;

PERCY, JM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (07) :757-758

[7] 2,2-DIFLUORO ENOL SILYL ETHERS - CONVENIENT PREPARATION AND APPLICATION TO THE SYNTHESIS OF A NOVEL FLUORINATED BRASSINOSTEROID [J].

JIN, FQ ;

XU, YY ;

HUANG, WY .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (07) :795-799

[8] LEWIS-ACID CATALYZED ALDOL-TYPE REACTION OF 1,1-DIFLUOROVINYL METHYL-ETHER DERIVATIVES [J].

KODAMA, Y ;

YAMANE, H ;

OKUMURA, M ;

SHIRO, M ;

TAGUCHI, T .

TETRAHEDRON, 1995, 51 (45) :12217-12228

[9] AN EFFICIENT AND GENERAL-METHOD FOR THE REFORMATSKY-TYPE REACTION OF CHLORODIFLUOROMETHYL KETONES WITH CARBONYL-COMPOUNDS GIVING ALPHA,ALPHA-DIFLUORO BETA-HYDROXY KETONES [J].

KUROBOSHI, M ;

ISHIHARA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (02) :428-437

[10]

Norley M, 1996, SYNLETT, P900