TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE PROMOTED CHEMOSELECTIVE REACTIONS OF ACYCLIC ACETALS IN THE PRESENCE OF CYCLIC ACETALS

被引:18
作者
KIM, S
DO, JY
KIM, SH
KIM, DI
机构
[1] Department of Chemistry, Korea Advanced Institute of Science and Technology
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 17期
关键词
D O I
10.1039/p19940002357
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Trimethylsilyl trifluoromethanesulfonate promoted chemoselective reactions of acyclic acetals with allyltrimethylsilane, allyltributyltin, a silyl enol ether, tributyltin hydride, trimethylsilyl azide and trimethylsilyl cyanide have been achieved in the presence of cyclic acetals.
引用
收藏
页码:2357 / 2358
页数:2
相关论文
共 17 条
[1]   THE ORIGIN OF STEREOSELECTIVE OPENING OF CHIRAL DIOXANE AND DIOXOLANE ACETALS - SOLUTION STRUCTURE OF THEIR LEWIS ACID COMPLEXES [J].
DENMARK, SE ;
WILLSON, TM ;
ALMSTEAD, NG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9258-9260
[2]  
GREENE TW, 1981, PROTECTIVE GROUPS OR
[3]   REDUCTION OF ACTIVATED KETALS WITH BORANE-DIMETHYL SULFIDE [J].
HUNTER, R ;
BARTELS, B ;
MICHAEL, JP .
TETRAHEDRON LETTERS, 1991, 32 (08) :1095-1098
[4]   ALLYLATION USING ORGANOBORATES AND ACTIVATED ACETALS [J].
HUNTER, R ;
TOMLINSON, GD .
TETRAHEDRON LETTERS, 1989, 30 (15) :2013-2016
[5]   ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .10. ALDOL-TYPE REACTIONS - PREPARATION OF A NONACETIC ACID INTERMEDIATE [J].
JOHNSON, WS ;
EDINGTON, C ;
ELLIOTT, JD ;
SILVERMAN, IR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (24) :7588-7591
[6]   A NOVEL METHOD FOR SELECTIVE DIOXOLANATION OF KETONES IN THE PRESENCE OF ALDEHYDES [J].
KIM, S ;
KIM, YG ;
KIM, DI .
TETRAHEDRON LETTERS, 1992, 33 (18) :2565-2566
[7]   REVERSE CHEMOSELECTIVITY IN THE COMPETITIVE ADDITION OF THALLIUM ATE COMPLEXES TO ENONES AND KETONES [J].
MARKO, IE ;
LEUNG, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (01) :371-372
[8]   CHEMOSELECTIVE CARBONYL ALKYLATION AND REDUCTION OF ALDEHYDES OR KETONES [J].
MARUOKA, K ;
ARAKI, Y ;
YAMAMOTO, H .
TETRAHEDRON LETTERS, 1988, 29 (25) :3101-3104
[9]   CHEMOSELECTIVE FUNCTIONALIZATION OF MORE HINDERED ALDEHYDE CARBONYLS WITH THE METHYLALUMINUM BIS(2,6-DIPHENYLPHENOXIDE)/ALKYLLITHIUM SYSTEM [J].
MARUOKA, K ;
SAITO, S ;
CONCEPCION, AB ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :1183-1184
[10]   A NOVEL CONCEPT FOR REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN LEWIS ACID PROMOTED [3+4] ANNULATION REACTIONS [J].
MOLANDER, GA ;
CAMERON, KO .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2617-2619