Abstract
AbstractThe sulfonium salts derived from the Baylis‐Hillman bromides have been successfully employed for the selective cycloproporanation of arylidene indane‐1,3‐diones to synthesize densely substituted spiro‐cyclopropanes in good to excellent yields (upto 94 %). Products were obtained mostly in 1:1 diastereomeric ratio and were isolated in pure form. Diastereoselectivity has been improved by using suitably substituted starting materials. In this case a formal [2+1] annulation reaction competes over a probable [3+2] cycloaddition reaction. The reaction proceeds through a Michael initiated ring closure process of S‐ylides to the activated olefins for the formation of structurally strained spiro‐cyclopropanes.
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