Tetrahedron p. 4559 - 4574 (1993)
Update date:2022-08-17
Topics:
Hackmann, Claus
Schaefer, Hans J.
A method for the synthesis of γ-butyrolactones 6 is described in which the key step is a free-radical cyclization of α-bromoacetals 4 to 2-alkoxytetrahydrofurans 5 in 54-93percent yield induced by activated chromium(II)-acetate.Four new methods have been developed in order to activate the transition metal.Two of them require only catalytic amounts of chromium(II)-acetate, because it can be regenerated in situ chemically or electrochemically.The diastereoselectivity of the cyclization depends on the substitution pattern of 4 and ranges between 30.4:1 and 1:54.8.
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