Highly regioselective and stereoselective allylation of aldehydes via palladium-catalyzed in situ hydrostannylation of allenes

被引:41
作者
Chang, HM [1 ]
Cheng, CH [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
关键词
D O I
10.1021/ol0064563
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Highly regio and stereoselective allylation of aldehydes by allenes proceeds smoothly in aqueous/organic media in the presence of PdCl2-(PPh3)(2), HCl, and SnCl2. The reaction likely occurs via hydrostannylation of allenes and allylation of aldehydes by the in situ generated allyltrichlorotins to afford the final products.
引用
收藏
页码:3439 / 3442
页数:4
相关论文
共 35 条
[1]   Palladium-indium mediated Barbier-type allylation of aldehydes with allenes [J].
Anwar, U ;
Grigg, R ;
Rasparini, M ;
Savic, V ;
Sridharan, V .
CHEMICAL COMMUNICATIONS, 2000, (08) :645-646
[2]   Palladium catalysed cyclisation-Barbier-type allylation cascades [J].
Anwar, U ;
Grigg, R ;
Sridharan, V .
CHEMICAL COMMUNICATIONS, 2000, (11) :933-934
[3]   A new preparative method for allylic indium(III) reagents by reductive transmetalation of π-allylpalladium(II) with indium(I) salts [J].
Araki, S ;
Kamei, T ;
Hirashita, T ;
Yamamura, H ;
Kawai, M .
ORGANIC LETTERS, 2000, 2 (06) :847-849
[4]   Palladium-catalyzed synthesis of 1,3-dienes from allenes and organic halides [J].
Chang, HM ;
Cheng, CH .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) :1767-1773
[5]   ALLYLIC SULFONES AS ALLYL ANION EQUIVALENTS - HOMOALLYLIC ALCOHOLS FROM METAL-CATALYZED REACTIONS OF SULFONES WITH ALDEHYDES AND KETONES [J].
CLAYDEN, J ;
JULIA, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (16) :1905-1906
[6]  
COLLMAN JP, 1987, PRINCIPLES APPLICATI, pCH19
[7]  
HECK RF, 1985, PALLADIUM REAGENTS O, P117
[8]  
HEGEDUS LS, 1984, COMPREHENSIVE CARBAN, P30
[9]   DIASTEREOGENIC ADDITION OF CROTYLMETAL COMPOUNDS TO ALDEHYDES [J].
HOFFMANN, RW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (08) :555-566
[10]  
Malleron J.-L., 1997, HDB PALLADIUM CATALY, DOI DOI 10.1002/anie.201700889