Palladium-Catalyzed Allylation of Aryl Halides with Homoallyl Alcohols Bearing a Trisubstituted Double Bond: Application to Chirality Transfer from Hydroxylated Carbon to Benzylic One

被引：16
|
作者：
Wakabayashi, Ryota [1 ]
Fujino, Daishi [1 ,2 ]
Hayashi, Sayuri [1 ]
Yorimitsu, Hideki [1 ,2 ]
Oshima, Koichiro [1 ]
机构：
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan
[2] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 13期
关键词：
CROSS-COUPLING REACTION; RETRO-ALLYLATION; ORGANIC-SYNTHESIS; CLEAVAGE; BROMIDES; COMPLEX; ALLYLTRIFLUOROSILANES; HYDROSILYLATION; ELIMINATION; CYCLIZATION;
D O I：
10.1021/jo100857d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile route to homoallyl alcohols bearing a trisubstituted double bond has been devised. The palladium-catalyzed reactions of aryl halides with the alcohols thus synthesized result in regiospecific allyl transfer from the alcohols to aryl halides via retro-allylation, providing allylarenes having two substituents at the 1 and 2 positions of the allyl moiety. Optically active homoallyl alcohols transfer their chirality at the hydroxylated carbon to the benzylic carbon of the product.
引用
收藏
页码：4337 / 4343
页数：7
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