Tetrahedron Letters

Substituted perhydrofuropyrans: easy preparation from 2-chloromethyl-3-(2-methoxyethoxy) propene through 3-methylene-1, 6-diols

E Lorenzo, F Alonso, M Yus

Index: Lorenzo, Emilio; Alonso, Francisco; Yus, Miguel Tetrahedron Letters, 2000 , vol. 41, # 10 p. 1661 - 1665

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Citation Number: 31

Abstract

The reaction of 2-chloromethyl-3-(2-methoxyethoxy) prop-1-ene (1) with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E1= R1R2CO) in THF at− 78 to 0° C, followed by treatment with an epoxide [E2= R3R4C (O) CHR5] at 0 to 20° C leads, after hydrolysis, to the expected unsaturated diols 2. When some compounds 2 (2e–h) are successively hydroborated (BH3· THF) and oxidised ...