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2-Chloromethyl-3-(2-methoxyethoxy)propene: Naphthalene-catalysed lithiation and reaction towards electrophiles

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
39
Issue
20
Identifiers
DOI: 10.1016/s0040-4039(98)00476-6

Abstract

Abstract The reaction of the title compound ( 1) with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of an electrophile [E 1 +=Bu tCHO, Et 2CO, (CH 2) 5CO, PhCOMe, Me 3SiCl] in THF at −78 to −30°C, followed by treatment with a second electrophile [E 2 +=Bu tCHO, Me 2CO, Et 2CO, (CH 2) 4CO, (CH 2) 5CO, Bu tCOMe, Bu t 2CO, PhCHNPh, Me 3SiCl, D 2O] at −30°C to room temperature leads, after hydrolysis, to the expected compounds 2. For carbonyl derivatives, compounds 2 were successively hydroborated (BH 3·THF) and oxidised [33% H 2O 2 and then PCC or RuCl 2(PPh 3) 3] to give directly the corresponding perhydrofurofurans 4.

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