Gallium-mediated allyl transfer from bulky homoallylic alcohol to aldehydes via retro-allylation:: Stereoselective synthesis of both erythro- and threo-homoallylic alcohols

被引：36

作者：

Hayashi, S ^{[1
]}

Hirano, K ^{[1
]}

Yorimitsu, H ^{[1
]}

Oshima, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 16期

关键词：

D O I：

10.1021/ol0515199

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Retro-allylation of bulky gallium homoallylic alkoxides occurs to generate (Z)- and (E)-crotylgallium reagents stereospecifically, starting from erythro- and threo-homoallylic alcohols, respectively. The (Z)- and (E)-crotylgallium reagents immediately reacted with aromatic aldehydes to afford the corresponding erythro- and threo-homoallylic alcohols, respectively.

引用

页码：3577 / 3579

页数：3

共 3 条

[1] Gallium-mediated allyl transfer from bulky homoallyl alcohol to aldehydes or alkynes:: Control of dynamic σ-allylgalliums based on retro-allylation reaction
Hayashi, Sayuri
Hirano, Koji
Yorimitsu, Hideki
Oshima, Koichiro
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (1-3) : 505 - 513
[2] Rhodium-catalyzed allyl transfer from homoallyl alcohols to aldehydes via retro-allylation followed by isomerization into ketones
Takada, Yuko
Hayashi, Sayuri
Hirano, Koji
Yorimitsu, Hideki
Oshima, Koichiro
ORGANIC LETTERS, 2006, 8 (12) : 2515 - 2517
[3] New and stereoselective synthesis of 1,4-disubstituted buten-4-ols (homoallylic alcohol α-adducts) from the corresponding γ-isomers (3,4-disubstituted buten-4-ols) via an acid-catalyzed allyl-transfer reaction with aldehydes
Sumida, S
Ohga, M
Mitani, J
Nokami, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) : 1310 - 1313

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