Novel 1,3-dipolar cycloaddition reactions of calix[4]bis(spirodienones): synthesis of isoxazolidine derived macrocycles |
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Authors: | V.B. Ganga R. Luxmi Varma |
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Affiliation: | a Organic Chemistry Section, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695 019, India b Analytical Science Discipline, Central Salt and Marine Chemicals Research Institute, Bhavnagar 364 002, India |
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Abstract: | Calix[4]bis(spirodienones) can perform as either 4π or 2π components in cycloaddition reactions with various carbo- and hetero-dienophiles and with 1,2-benzoquinones leading to the formation of highly functionalized macrocycles. In this Letter we report, highly regio- and stereoselective 1,3-dipolar cycloaddition reactions of a bis(spirodienone) derivative of calix[4]arene with nitrones that provide easy access to isoxazolidine derived macrocycles in excellent yields. These isoxazolidine derivatives can be considered as direct precursors of 1,3-amino alcohols. |
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Keywords: | Calix[4]bis(spirodienone) C,N-Diarylnitrone 1,3-Dipolar cycloaddition Isoxazolidine |
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