STEREOCHEMISTRY IN THE PROTONATION OF ENOLATES GENERATED FROM 2-SUBSTITUTED 2-CYCLOPENTEN-1-ONES BY THE 1, 4-ADDITION OF TRIALKYLSILYL AND TRIBUTYLSTANNYL ANIONS

Shinya Kusuda Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466, Japan

Yoshio Ueno Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466, Japan

Takeshi Toru Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466, Japan

Abstract

The 1, 4-addition of trialkylsilyl anions to 2-(phenylseleno)-2-cyclopenten-1-one affords trans cyclopentanone derivatives. A similar trans selectivty was observed in the protonation of enolates derived from phenylseleno-or phenylthiocyclopentenones by the addition of the vinyl anion corresponding to the prostaglandin ω-chain. On the other hand, the 1, 4-additions of trialkylsilyl and tributylstannyl anions to 2-(2-propenyl)-2-cyclopenten-1-one lead to a predominant formation of the cis compounds.

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STEREOCHEMISTRY IN THE PROTONATION OF ENOLATES GENERATED FROM 2-SUBSTITUTED 2-CYCLOPENTEN-1-ONES BY THE 1, 4-ADDITION OF TRIALKYLSILYL AND TRIBUTYLSTANNYL ANIONS

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STEREOCHEMISTRY IN THE PROTONATION OF ENOLATES GENERATED FROM 2-SUBSTITUTED 2-CYCLOPENTEN-1-ONES BY THE 1, 4-ADDITION OF TRIALKYLSILYL AND TRIBUTYLSTANNYL ANIONS

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