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Asymmetric 1,3-dipolar cycloadditions to 5-menthyloxy-2[5H]-furanones.

โœ Scribed by Ben de Lange; Ben L. Feringa

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
254 KB
Volume
29
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Cycloadditions of various 1,3-dipolar reagents to chiral butenolides 1 and 2 proceed with diastereomeric excess of 20-100%. Recently we reported a new class of C-4 and C-5 chiral synthons based on

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## Abstract Benzonitrile oxide cycloadds to the C๏ฃพC bond of substituted 4,5โ€dihydroโ€3โ€methyleneโ€2(3__H__)โ€furanones 1aโ€“1g. Thus, (__E__)โ€1a and (__E__)โ€1b are converted into the corresponding isoxazolinespirodihydrofuranones (4__RS__,5__RS__)โ€2a and (4__RS__,5__RS__)โ€2b, and (__E__)โ€1c is converted