New, practical and effective sources of fluoride ion for desilylation to form carbon anions

被引:31
作者
Busch-Petersen, J [1 ]
Bo, YX [1 ]
Corey, EJ [1 ]
机构
[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
关键词
D O I
10.1016/S0040-4039(99)00166-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Suspensions of powdered glassy solids prepared by fusion of 1 : 1 mixtures of CsF-CsOH and CsF-CsCl effectively catalyze the generation of enolates, acetylide and other anions from trimethylsilylated precursors. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2065 / 2068
页数:4
相关论文
共 13 条
[1]   SYNTHESES, PROPERTIES, AND STRUCTURES OF ANHYDROUS TETRAMETHYLAMMONIUM FLUORIDE AND ITS 1-1 ADDUCT WITH TRANS-3-AMINO-2-BUTENENITRILE [J].
CHRISTE, KO ;
WILSON, WW ;
WILSON, RD ;
BAU, R ;
FENG, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) :7619-7625
[2]   TOTAL SYNTHESIS OF (+/-)-FUMAGILLIN [J].
COREY, EJ ;
SNIDER, BB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (07) :2549-&
[3]   TETRABUTYLAMMONIUM DIFLUOROTRIPHENYLSTANNATE AS A NEW ANHYDROUS SYNTHETIC EQUIVALENT TO TBAF [J].
GINGRAS, M .
TETRAHEDRON LETTERS, 1991, 32 (50) :7381-7384
[4]   REACTIVE ENOLATES FROM ENOL SILYL ETHERS [J].
KUWAJIMA, I ;
NAKAMURA, E .
ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (06) :181-187
[5]  
Middleton W. J., 1976, [No title captured], Patent No. [US3940402, 3940402]
[6]   SUPERANIONS .5. TRIS(DIALKYLAMINO)SULFONIUM ENOLATES - SYNTHESIS, STRUCTURE, AND REACTIONS [J].
NOYORI, R ;
NISHIDA, I ;
SAKATA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (06) :1598-1608
[7]   TRIS(DIALKYLAMINO)SULFONIUM ENOLATES [J].
NOYORI, R ;
NISHIDA, I ;
SAKATA, J ;
NISHIZAWA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (03) :1223-1225
[8]  
PAQUETTE LA, 1995, ENCY REAGENTS ORGANI, P4728
[9]   Utilization of tetrabutylammonium triphenyldifluorosilicate as a fluoride source for silicon-carbon bond cleavage [J].
Pilcher, AS ;
DeShong, P .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :6901-6905
[10]   STABLE PHOSPHAZENIUM IONS IN SYNTHESIS - AN EASILY ACCESSIBLE, EXTREMELY REACTIVE NAKED FLUORIDE SALT [J].
SCHWESINGER, R ;
LINK, R ;
THIELE, G ;
ROTTER, H ;
HONERT, D ;
LIMBACH, HH ;
MANNLE, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (10) :1372-1375