A new practical synthesis of germylalkoxydienes, acylgermanes and ethynylgermanes from α,β-unsaturated and α-phenyl acetals

被引:4
作者
Allasia, S [1 ]
Deagostino, A [1 ]
Prandi, C [1 ]
Zavattaro, C [1 ]
Venturello, P [1 ]
机构
[1] Univ Turin, Dipartimento Chim Gen & Organ Applicata, I-10125 Turin, Italy
来源
SYNTHESIS-STUTTGART | 2005年 / 20期
关键词
acetals; organometallic reagents; superbases; germyldienes; acylgermanes;
D O I
10.1055/s-2005-918414
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The treatment of alpha,beta-unsaturated acetals 1a-f with LIC-KOR base (equimolar mixture of n-BuLi and tert-BuOK) produces alpha-metalated alkoxy-1,3-dienes that easily react with halotrialkyl-and halotriarylgermanes producing substituted (Z)-alkoxyvinylgermanes 2a-i in good yields. Functionalized dienyl derivatives can be transformed into the corresponding acylgermanes 3a-d under mild acidic hydrolytic conditions. Furthermore, the lithium-potassium mixed reagent promotes the conversion of the a-phenyl acetal 4 into trimethyl(2-phenylethynyl)germane (5).
引用
收藏
页码:3627 / 3631
页数:5
相关论文
共 35 条
[1]  
[Anonymous], 1999, J CHEM EDUC
[2]   ALPHA-METHOXYVINYLLITHIUM AND RELATED METALATED ENOL ETHERS - PRACTICAL REAGENTS FOR NUCLEOPHILIC ACYLATION [J].
BALDWIN, JE ;
HOFLE, GA ;
LEVER, OW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (22) :7125-7127
[3]   A facile synthesis of 2,2,6,6-tetramethyl-2-germa-3,5-heptandione:: The preparation and characterization of the first germa-β-diketonate copper(II) complex [J].
Banger, KK ;
Birringer, C ;
Claessen, RU ;
Lim, P ;
Toseano, PJ ;
Welch, JT .
ORGANOMETALLICS, 2001, 20 (22) :4745-4748
[4]   PREPARATION AND SYNTHETIC APPLICATIONS OF LITHIUM DI(ALPHA-METHOXYVINYL)CUPRATE [J].
CHAVDARIAN, CG ;
HEATHCOCK, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (13) :3822-3823
[5]   Radical cyclizations of acylgermanes. New reagent equivalents of the carbonyl radical acceptor synthon [J].
Curran, DP ;
Diederichsen, U ;
Palovich, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) :4797-4804
[6]   Cross-coupling reaction:: stereoselective synthesis of (E)-aryl or heteroarylvinylgermanes [J].
David-Quillot, F ;
Thibonnet, J ;
Marsacq, D ;
Abarbri, M ;
Duchêne, A .
TETRAHEDRON LETTERS, 2000, 41 (51) :9981-9984
[7]   α,β-unsaturated acetals in synthesis [J].
Deagostino, A ;
Prandi, C ;
Venturello, P .
CURRENT ORGANIC CHEMISTRY, 2003, 7 (09) :821-839
[8]   Highly stereospecific, palladium-catalyzed cross-coupling of alkenylsilanols [J].
Denmark, SE ;
Wehrli, D .
ORGANIC LETTERS, 2000, 2 (04) :565-568
[9]   Highly stereospecific, cross-coupling reactions of alkenylsilacyclobutanes [J].
Denmark, SE ;
Choi, JY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) :5821-5822
[10]  
Denmark SE, 2000, SYNTHESIS-STUTTGART, P999