Enantioselective preparation of 3,4,5-trisubstituted-4,5-dihydroisoxazolesand 4-substituted-5,6-dihydro-4H[1,2]-oxazines by nitrile oxide cycloaddition to alpha-silyl allyl alcohols

Authors
Kamimura, A Kaneko, Y Ohta, A Kakehi, A Matsuda, H Kanemasa, S
Citation
A. Kamimura et al., Enantioselective preparation of 3,4,5-trisubstituted-4,5-dihydroisoxazolesand 4-substituted-5,6-dihydro-4H[1,2]-oxazines by nitrile oxide cycloaddition to alpha-silyl allyl alcohols, TETRAHEDR L, 40(23), 1999, pp. 4349-4352
Citations number
39
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
23
Year of publication
1999
Pages
4349 - 4352
Database
ISI
SICI code
0040-4039(19990604)40:23<4349:EPO3>2.0.ZU;2-D
Abstract
Regio- and stereoselective 1,3-dipolar cycloaddition of nitrile oxide to op tically active alpha-silyl allyl alcohol provides a useful preparation of 3 ,4,5-trisubstituted 4,5-dihydroisoxazoles, which are readily converted into chiral 4-substituted 5,6-dihydro-4H-[1,2]-oxazines in 73-100% yields on tr eatment with TBAF. (C) 1999 Elsevier Science Ltd. All rights reserved.