American Chemical Society
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Reductive Cyclizations of Hydroxysulfinyl Ketones:  Enantioselective Access to Tetrahydropyran and Tetrahydrofuran Derivatives

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journal contribution
posted on 2003-09-06, 00:00 authored by M. Carmen Carreño, Renaud Des Mazery, Antonio Urbano, Françoise Colobert, Guy Solladié
The stereocontrolled formation of cis-2,5-disubstituted tetrahydrofurans and cis-2,6-disubstituted tetrahydropyrans is achieved from enantiopure ketosulfinyl esters by reduction, Weinreb's amide, and ketone formation, followed by the reductive cyclization (Et3SiH/TMSOTf) of the resulting hydroxysulfinyl ketones. The sulfoxide-bearing heterocycles were transformed into two natural products, (−)-centrolobine (1) and both enantiomers of cis-(6-methyltetrahydropyran-2-yl)acetic acid (2).