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Stereoselective syntheses of 2-subtituted perhydrofuro[2,3b]furans

Published on Jan 1, 1988in Tetrahedron2.379
· DOI :10.1016/S0040-4020(01)81719-1
Jan Vader6
Estimated H-index: 6
,
Rimco Koopmans1
Estimated H-index: 1
+ 2 AuthorsKerk van der S. M2
Estimated H-index: 2
Abstract
Abstract New reagents for the stereoselective synthesis of 2-substituted perhydrofuro[2,3b]furanas are described. Ia the successful approach towards the latter compounds, the key steps were the addition of a aonolithio-2α-methoxy-3β-[(phenylsulfonyl)-methyilperhydrofuran to an aldehyde and a dilithio-2α-methoxy-3β-[(pheaylsulfonyl)-methyl]perhydrofuran to a carboxy1 derivative, respectively. The structures and conformations of the 2-tert-butylmtyl- and Z-isopropylper-hydrofuro [2,3b]furans were examined by means of 1 H-NMR double resonance and the 2D-NOE spectroscopy.
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