Tetrahedron p. 1953 - 1960 (1996)
Update date:2022-08-05
Topics:
Fukuzawa, Shin-Ichi
Furuya, Hideki
Tsuchimoto, Teruhisa
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 alkylation followed by cyclization; a substituted cyclobutanol was formed in poor yield.
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(1999)