ChemInform Abstract: 1,3-Dipolar Cycloaddition Reactions of Nitrones with Alkyl Vinyl Ethers Catalyzed by Chiral Oxazaborolidines.
Abstract
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ChemInform Abstract
It is found that 1,3-dipolar cycloadditions of various nitrones with ethyl vinyl ether are catalyzed by chiral oxazaborolidines. The reaction proceeds with complete regioselectivity but with poor stereoselectivity and very low enantioselectivity (ca. 0% e.e.). With rigid (Z)-alkyl vinyl ether drastically improved stereoselectivity is observed. Starting from the nitrone (VIII) a cycloadduct with moderate enantioselectivity can be obtained.
