A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a delta-carbon radical adds intramolecularly to the carbonyl group of an aldehyde. The delta-carbon radicals can be efficiently produced from the tin hydride mediated deselenenylation of 5-phenylseleno-3-oxapentanals which were easily prepared starting from commercially available enantiopure epoxides or chlorohydrins
Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols.
TIECCO, Marcello;TESTAFERRI, Lorenzo;MARINI, Francesca;STERNATIVO, Silvia;SANTI, Claudio;BAGNOLI, Luana;TEMPERINI, Andrea
2007
Abstract
A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a delta-carbon radical adds intramolecularly to the carbonyl group of an aldehyde. The delta-carbon radicals can be efficiently produced from the tin hydride mediated deselenenylation of 5-phenylseleno-3-oxapentanals which were easily prepared starting from commercially available enantiopure epoxides or chlorohydrinsFile in questo prodotto:
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