Cascade triple-aldehyde addition of 1,2,3,4-tetrakis(pinacolatoboryl)but-2-ene: stereoselective synthesis of 2,3-bis(alkylidene)alkane-1,5-diols.

Cascade triple-aldehyde addition of 1,2,3,4-tetrakis(pinacolatoboryl)but-2-ene: stereoselective synthesis of 2,3-bis(alkylidene)alkane-1,5-diols. Research Abstract Details 

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Cascade triple-aldehyde addition of 1,2,3,4-tetrakis(pinacolatoboryl)but-2-ene: stereoselective synthesis of 2,3-bis(alkylidene)alkane-1,5-diols. Abstract Text:

Masaki Shimizu,Katsuhiro Shimono,Tamejiro Hiyama,Masaki Shimizu,Katsuhiro Shimono,Tamejiro Hiyama,

Treatment of (Z)-1,2,3,4-tetrakis(pinacolatoboryl)but-2-ene, prepared from 2,3-bis(pinacolatoboryl)buta-1,3-diene and bis(pinacolato)diboron, with three molar equivalents of aldehyde in toluene at 100 degrees C gave the 2,3-bis(alkylidene)alkane-1,5-anti-diol as a single stereoisomer. The reaction is applicable to both aromatic and alpha-unbranched aliphatic aldehydes. The 1,5-anti-diols were also synthesized by the one-pot preparation/triple-aldehyde addition of the tetraborylated butene. Experimental results for the stepwise treatment of the butene with two types of aldehydes suggest that the rate-determining step of the triple-aldehyde addition is the third allylation.

Cascade triple-aldehyde addition of 1,2,3,4-tetrakis(pinacolatoboryl)but-2-ene: stereoselective synthesis of 2,3-bis(alkylidene)alkane-1,5-diols. Publishing Authors By Initials

M Shimizu,K Shimono,T Hiyama,M Shimizu,K Shimono,T Hiyama,

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Cascade triple-aldehyde addition of 1,2,3,4-tetrakis(pinacolatoboryl)but-2-ene: stereoselective synthesis of 2,3-bis(alkylidene)alkane-1,5-diols. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Chemistry, an Asian journal

VOLUME: 2

Page Numbers: 1142-9

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ISSN: 1861-471X

DAY: 3

MONTH: Sep

YEAR: 2007

Cascade triple-aldehyde addition of 1,2,3,4-tetrakis(pinacolatoboryl)but-2-ene: stereoselective synthesis of 2,3-bis(alkylidene)alkane-1,5-diols. Information

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LANGUAGE: eng

NlmUniqueID: 101294643

Cascade triple-aldehyde addition of 1,2,3,4-tetrakis(pinacolatoboryl)but-2-ene: stereoselective synthesis of 2,3-bis(alkylidene)alkane-1,5-diols. Keywords Mesh Terms:

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AFFILIATION: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan. shimizu@npc05.kuic.kyoto-u.ac.jp

Country: Germany

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