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Lewis acid stereocontrolled additions of a silyl ketene acetal to 2,3-di-O-isopropylidene-d-glyceraldehyde nitrones. Synthesis ofl-isoxazolidinyl nucleosides

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
41
Issue
48
Identifiers
DOI: 10.1016/s0040-4039(00)01674-9

Abstract

Abstract The reaction of O-methyl- O- tert-butyldimethylsilyl ketene acetal with N-benzyl and N-methyl-2,3- O-isopropylidene- d-glyceraldehyde nitrones in the presence of boron trifluoride etherate afforded the corresponding isoxazolidin-5-ones in excellent yields and anti-selectivities. The obtained compounds were used as key intermediates for the synthesis of isoxazolidinyl nucleosides of the l-series.

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