Tetrahedron

Alkylation-annulation of halo esters with organometallic reagent/SmI 2 couple leading to cycloalkanols: A facile cyclopropanol synthesis from a 3-halo ester

S Fukuzawa, H Furuya, T Tsuchimoto

Index: Fukuzawa, Shin-Ichi; Furuya, Hideki; Tsuchimoto, Teruhisa Tetrahedron, 1996 , vol. 52, # 6 p. 1953 - 1960

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Citation Number: 19

Abstract

Transformation of a 3-halo ester to cyclopropanols has been accomplished in excellent yields under mild conditions employing a coupled reagent of samarium (II) diiodide with organometallic reagents. 5-and 6-Halo esters were also transformed into cyclopentanols and cyclohexanols, respectively, in low to moderate yields. The reaction with a 4-halo ester gave 2, 2-disubstituted tetrahydrofuran as a major product that resulted from double ...