Diastereoselective Syntheses of Highly Substituted Methyl Tetrahydrofuran-3-carboxylates by Reactions of γ-Lactols with Silylated Nucleophiles

DOI: 10.1021/jo00246a011

Source and publish data:

Journal of Organic Chemistry p. 2450 - 2456 (1988)

Update date:2022-07-29

Topics: Reactions Diastereoselective Highly substituted γ-lactols

Authors:

Brueckner, Christiane

Holzinger, Hiltrud

Reissig, Hans-Ulrich

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Article abstract of DOI:10.1021/jo00246a011

Hydroxyalkylation of enolates generated from methyl 2-siloxycyclopropanecarboxylates 1 followed by fluoride-induced ring opening gives γ-lactols as key intermediates.Their reduction with triethylsilane / BF3*OEt2 affords methyl tetrahydrofuran-3-carboxyla

Full text of DOI:10.1021/jo00246a011

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