A highly diastereoselective approach to tetrahydrofurans via [3+2] cycloadditions of silylmethyl-substituted cyclopropanes with aldehydes and ketones |
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| Authors: | Archana Gupta |
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| Institution: | Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India |
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| Abstract: | An efficient and highly diastereoselective synthesis of highly substituted tetrahydrofurans from the reaction of a vicinal t-butyldiphenylsilylmethyl-substituted cyclopropyl diester with aldehydes and ketones has been developed. The 2,5-cis-disubstitution predominates over the 2,5-trans-disubstitution by as much as 12:1. The reaction with cyclic ketones generates spiro-fused tetrahydrofurans in good yields. |
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| Keywords: | 1 3-Dipole Cycloaddition 2 3 5- and 2 3 4 5-Substituted tetrahydrofurans |
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