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

Authors
Merino, P del Alamo, EM Bona, M Franco, S Merchan, FL Tejero, T Vieceli, O
Citation
P. Merino et al., Lewis acid stereocontrolled additions of a silyl ketene acetal to 2,3-di-O-isopropylidene-D-glyceraldehyde nitrones. Synthesis of L-isoxazolidinyl nucleosides, TETRAHEDR L, 41(48), 2000, pp. 9239-9243
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
48
Year of publication
2000
Pages
9239 - 9243
Database
ISI
SICI code
0040-4039(20001125)41:48<9239:LASAOA>2.0.ZU;2-E
Abstract
The reaction of O-methyl-O-tert-butyldimethylsilyl ketene acetal with N-ben zyl and N-methyl-2,3-O-isopropylidene-D-glyceraldehyde nitrones in the pres ence of boron trifluoride etherate afforded the corresponding isoxazolidin- 5-ones in excellent yields and anti-selectivities. The obtained compounds w ere used as key intermediates for the synthesis of isoxazolidinyl nucleosid es of the L-series. (C) 2000 Elsevier Science Ltd. All rights reserved.