Asymmetric Hosomi - Sakurai Reaction of Allylsilanes Containing Arabinose-Derived Alcohols as Chiral Auxiliaries

Tony K.M. Shing, Lian Hai Li

研究成果: Article

19 引用 (Scopus)

抜粋

Five enantiopure allylsilanes la-e have been prepared, with arabinose-derived alcohols methyl and benzyl 3,4-O-isopropylidene- and 3,4-O-methylene-β-L-arabinopyranosides as chiral auxiliaries, and subjected to the asymmetric Hosomi - Sakurai reaction. The effect of Lewis acid on the stereochemical outcome of the reaction was investigated, and BF3 was found to exhibit higher enantioselectivity than that of SnCl4 or TiCl4. The reaction of benzyl 2-O-(allyldimethylsilyl)-3,4-O-isopropylidene-β-L-arabinopyranoside (1b) with n-decanal gave the highest ee (45%) in the presence of BF3. The steric effect of the chiral auxiliary on the asymmetric Hosomi-Sakurai reaction is demonstrated for the first time although the stereogenic center is remote from the reaction site.

元の言語English
ページ(範囲)1230-1233
ページ数4
ジャーナルJournal of Organic Chemistry
62
発行部数5
DOI
出版物ステータスPublished - 1997 1 1

ASJC Scopus subject areas

  • Organic Chemistry

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