Beceived inlISA 6 Jnly1970; received inI0Kfor~blicetiom 3 Septe&er IgO) Tbe 1,3-dipolar cycloadditioa reectioe has been the sobject of tiaz eabaustive ard elegant iaveatigationa of Eluiagen sad w-a~rkers.~ Tkse reactions shap all the cbarecteristics of coacerted reactions, iacluding stereospecificit
Stereoselective [6 + 4] cycloadditions of methylfulvene and phenylfulvene to tropone
β Scribed by K.N. Houk; L.J. Luskus; N.S. Bhacca
- Publisher
- Elsevier Science
- Year
- 1972
- Tongue
- French
- Weight
- 181 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
We recently reported the periaelective formation of 2:l adduct && in the reaction of tropone with dimethylfu1vene.l This observation of an unprecedented reaction of a fulvene as a 6~ addend has led us to investigate further the mechanism of this reaction.
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Cycloaddition of nitrile oxides to 4-vinyl-2-oxazoline 1 and to 4-vinyloxazolidine 2 afford diastereomeric mixtures of 2-isoxazolines in which the eryrhro product predominates (32-64% d.e.). In contrast, the cortesponding reactions with acyclic analogue 3 favoured the fhreoadducts and were less sele