Stereoselective Synthesis of (2E,4E)- and (2Z,4E)-2,4-Alkadienoates by the Ester Enolate Claisen Rearrangement of (E)-1-Alkyl-3-trimethylsilyl-2-propenyl Glycolates Followed by the Peterson Reaction

Toshio Sato,Hiromasa Kohama,Tamotsu Fujisawa,Hiroshi Tsunekawa

doi:10.1246/cl.1986.1553

Stereoselective Synthesis of (2E,4E)- and (2Z,4E)-2,4-Alkadienoates by the Ester Enolate Claisen Rearrangement of (E)-1-Alkyl-3-trimethylsilyl-2-propenyl Glycolates Followed by the Peterson Reaction

Toshio Sato, Hiromasa Kohama + Show 2 more

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https://doi.org/10.1246/cl.1986.1553

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Journal: Chemistry Letters	Publication Date: Sep 5, 1986
Citations: 19

Affiliation: Mie University

#Peterson Reaction #High Diastereoselectivity + Show 6 more

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Abstract

Abstract The ester enolate Claisen rearrangement of (E)-1-alkyl-3-trimethylsilyl-2-propenyl glycolates gave (E)-erythro-2-hydroxy-3-trimethylsilyl-4-alkenoates with high diastereoselectivity, which were stereoselectively converted into (2E,4E)- and (2Z,4E)-2,4-alkadienoates by the Peterson reaction.

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