Novel Lewis acid promoted reactions of allylsilane bearing bulky silyl substituents and aldehydes

被引:21
作者
Akiyama, T [1 ]
Nakano, M [1 ]
Kanatani, JY [1 ]
Ozaki, S [1 ]
机构
[1] EHIME UNIV, FAC ENGN, DEPT APPL CHEM, MATSUYAMA, EHIME 790, JAPAN
关键词
D O I
10.1246/cl.1997.385
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reported herein are two novel modes of reactions that were mediated by the proper choice of Lewis acid. Thus, by the influence of SnCl4, allyl-t-butyldimethylsilane reacted with aldehyde in 2:1 stoichiometry to afford a ketone derivative. In contrast, use of BF3 . OEt2 led to the formation of a 1,3-dioxane derivative, which is a 1:2 adduct.
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页码:385 / 386
页数:2
相关论文
共 20 条
[1]   STEREOSELECTIVE CONSTRUCTION OF TETRAHYDROFURAN BY TIN-(IV)-CHLORIDE PROMOTED [3+2]-CYCLOADDITION OF ALLYLSILANE TO ALPHA-KETO ESTER [J].
AKIYAMA, T ;
ISHIKAWA, K ;
OZAKI, S .
CHEMISTRY LETTERS, 1994, (03) :627-630
[2]   ASYMMETRIC-SYNTHESIS OF TETRAHYDROFURANS BY DIASTEREOSELECTIVE [3+2]-CYCLOADDITION OF ALLYLSILANES WITH ALPHA-KETO ESTERS BEARING AN OPTICALLY-ACTIVE CYCLITOL AS A CHIRAL AUXILIARY [J].
AKIYAMA, T ;
YASUSA, T ;
ISHIKAWA, K ;
OZAKI, S .
TETRAHEDRON LETTERS, 1994, 35 (45) :8401-8404
[3]   STEREOSELECTIVE CONSTRUCTION OF OXETANE BY TITANIUM(IV) CHLORIDE PROMOTED [2+2]-CYCLOADDITION OF ALLYLSILANE TO ALPHA-KETO ESTERS [J].
AKIYAMA, T ;
KIRINO, M .
CHEMISTRY LETTERS, 1995, (08) :723-724
[4]  
Akiyama T, 1996, SYNLETT, P1095
[5]   Tritylallyldimethylsilane-TiCl4 annulations to electron deficient olefins. Diastereomerically pure 3-substituted and 3,4-disubstituted cyclopentanols [J].
Brengel, GP ;
Meyers, AI .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3230-3231
[6]   [2+2]-CYCLOADDITION AND [3+2]-CYCLOADDITION OF TRIISOPROPYLALLYLSILANE TO ALPHA,BETA-UNSATURATED BICYCLIC LACTAMS [J].
BRENGEL, GP ;
RITHNER, C ;
MEYERS, AI .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5144-5146
[7]   SYNTHESIS OF 4-HALOTETRAHYDROPYRANS FROM ALLYLSILANES AND CARBONYL-COMPOUNDS IN THE PRESENCE OF LEWIS-ACIDS [J].
COPPI, L ;
RICCI, A ;
TADDEI, M .
TETRAHEDRON LETTERS, 1987, 28 (09) :973-976
[8]   5-MEMBERED RING ANNULATION VIA PROPARGYLSILANES AND ALLYLSILANES [J].
DANHEISER, RL ;
DIXON, BR ;
GLEASON, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6094-6097
[9]  
Fleming I., 1991, Comprehensive Organic Synthesis, V2, P563
[10]  
Fleming I., 1989, ORG REACTIONS, V37, P57