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

✍ Scribed by Akio Kamimura; Yukio Kaneko; Ayaki Ohta; Akikazu Kakehi; Haruhiko Matsuda; Shuji Kanemasa

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 241 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00688-7

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✦ Synopsis

Regio-and stereoselective 1,3-dipolar cycloaddition of nitrile oxide to optically active asilyl 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 treatment with TBAF.

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