Olefinic diols, prepared from (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde via olefination and hydrolysis, were converted into optically pure hydroxy substituted tetrahydrofuran derivatives by cyclization using N-phenylselenophtalimide and BF3. The PhSe group in the C-4 position of these tetrahydrofurans was then substituted by an allyl group using allyltributylstannane in the presence of AIBN. The selenium promoted cyclizations of the allyl tetrahydrofurans in which the OH and the allyl groups are trans to each other formed the enantiopure perhydrofuro[3,4-b]pyrans, while the cyclization of the allyl tetrahydrofurans in which the OH and the allyl groups are in cis gave rise to the perhydrofuro[3,4-b]furans. These bicyclic products were finally deselenenylated with triphenyltin hydride and AIBN.

Synthesis of enantiomerically pure perhydrofuro [3,4-b]pyrans and perydrofuro[3,4-b] furans

TIECCO, Marcello;TESTAFERRI, Lorenzo;BAGNOLI, Luana;TEMPERINI, Andrea;MARINI, Francesca;SANTI, Claudio;
2004

Abstract

Olefinic diols, prepared from (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde via olefination and hydrolysis, were converted into optically pure hydroxy substituted tetrahydrofuran derivatives by cyclization using N-phenylselenophtalimide and BF3. The PhSe group in the C-4 position of these tetrahydrofurans was then substituted by an allyl group using allyltributylstannane in the presence of AIBN. The selenium promoted cyclizations of the allyl tetrahydrofurans in which the OH and the allyl groups are trans to each other formed the enantiopure perhydrofuro[3,4-b]pyrans, while the cyclization of the allyl tetrahydrofurans in which the OH and the allyl groups are in cis gave rise to the perhydrofuro[3,4-b]furans. These bicyclic products were finally deselenenylated with triphenyltin hydride and AIBN.
2004
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11391/152129
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