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

Tony Kung Ming Shing, Lian Hai Li

Research output: Contribution to journalArticle

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
Externally publishedYes

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Arabinose
Alcohols
Lewis Acids
Enantioselectivity
Methanol
propylene
allylsilane
stannic chloride
titanium tetrachloride
decanaldehyde

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Asymmetric Hosomi - Sakurai Reaction of Allylsilanes Containing Arabinose-Derived Alcohols as Chiral Auxiliaries. / Shing, Tony Kung Ming; Li, Lian Hai.

In: Journal of Organic Chemistry, Vol. 62, No. 5, 01.01.1997, p. 1230-1233.

Research output: Contribution to journalArticle

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