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

Tony K.M. Shing, Lian Hai Li

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19 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1230-1233
Number of pages4
JournalJournal of Organic Chemistry
Volume62
Issue number5
DOIs
Publication statusPublished - 1997 Jan 1

ASJC Scopus subject areas

  • Organic Chemistry

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