TERT-BUTYLDIMETHYLSILYLDICHLOROMETHYLLITHIUM AS A DICHLOROMETHYLENE DIANION SYNTHON - 1,3-REARRANGEMENT OF SILYL GROUP FROM CARBON TO OXIDE

被引：35

作者：

SHINOKUBO, H ^{[1
]}

MIURA, K ^{[1
]}

OSHIMA, K ^{[1
]}

UTIMOTO, K ^{[1
]}

机构：

[1] KYOTO UNIV,FAC ENGN,DEPT IND CHEM,SAKYO KU,KYOTO 60601,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(00)91972-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

One-pot synthesis of R1CH(OSiMe2-t-Bu)CCl2CH(OH)R2 by successive addition of two different electrophiles has been achieved starting from tert-butyldimethylsilyldichloromethyltithium. Treatment of a THF solution of the tide carbanion with p-MeOC6H4CHO or n-BuCHO followed by an addition of HMPA and benzaldehyde gave the corresponding 1,3-diol monosilyl ether in 83% or 45% yield, respectively.

引用

页码：1951 / 1954

页数：4

共 23 条

[1] DIRECTED ORTHO METALATION OF SILYLOXYBENZAMIDES - ANION INDUCED O -] C SILICON REARRANGEMENT [J].

BILLEDEAU, RJ ;

SIBI, MP ;

SNIECKUS, V .

TETRAHEDRON LETTERS, 1983, 24 (42) :4515-4518

[2] SOME MOLECULAR-REARRANGEMENTS OF ORGANOSILICON COMPOUNDS [J].

BROOK, AG .

ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (03) :77-84

[3] STEREOCHEMISTRY OF FORMATION AND THERMAL REARRANGEMENT OF BETA-KETOSILANES [J].

BROOK, AG ;

MACRAE, DM ;

LIMBURG, WW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (21) :5493-&

[4]

BROOK AG, 1980, REARRANGEMENTS GROUN, V2, P149

[5] ALPHA-CHLORO-ALPHA-TRIMETHYLSILYL CARBANION, A REAGENT FOR HOMOLOGATION OF KETONES AND ALDEHYDES VIA ALPHA,BETA-EPOXYSILANES [J].

BURFORD, C ;

COOKE, F ;

EHLINGER, E ;

MAGNUS, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (13) :4536-4537

[6] SILICON-CONTAINING CARBANIONS .2. KETENE THIOACETAL SYNTHESIS VIA 2-LITHIO-2-TRIMETHYLSILYL-1,3-DITHIANE [J].

CAREY, FA ;

COURT, AS .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (12) :1926-&

[7] A PRACTICAL AND EFFICIENT SYNTHESIS OF ALPHA,BETA-UNSATURATED ACYLSILANES [J].

DANHEISER, RL ;

FINK, DM ;

OKANO, K ;

TSAI, YM ;

SZCZEPANSKI, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5393-5396

[8] FLUORIDE-ION CATALYZED ALDEHYDE ADDITION OF LABILE ALPHA-HALOCARBANION OR BETA-HALOCARBANION SPECIES GENERATED FROM THE CORRESPONDING ALPHA-HALO OR BETA-HALO ORGANOSILANES [J].

FUJITA, M ;

HIYAMA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :4085-4087

[9] WITTIG-TYPE REACTIONS OF 2-LITHIO-2-TRIMETHYLSILYL-1,3-DITHIAN AND RELATED REACTIONS [J].

JONES, PF ;

LAPPERT, MF ;

SZARY, AC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (20) :2272-2277

[10] 1,2-ADDITION OF DIMETHYL(PHENYL)SILYLLITHIUM TO CYCLIC ALPHA,BETA-UNSATURATED KETONES AND REGIOSPECIFIC GENERATION OF CYCLIC SILYL ENOL ETHERS THROUGH BROOK REARRANGEMENT OF THE 1,2-ADDITION PRODUCTS [J].

KOREEDA, M ;

KOO, S .

TETRAHEDRON LETTERS, 1990, 31 (06) :831-834

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