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Lewis Acid-Promoted Reactions of 3-Methoxy-N-(benzenesulfonyl)-1,4-benzoquinone Monoimine with Propenylbenzenes

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journal contribution
posted on 07.08.1998, 00:00 by Thomas A. Engler, Cynthia M. Scheibe
BF3·OEt2-promoted reactions of 4-N-(benzenesulfonyl)-3-methoxy-1,4-benzoquinone monoimine (5) with (E)-propenylbenzenes bearing strong electron-donating groups on their aromaric rings produce 2-aryl-6-methoxy-3-methyl-5-[N-(benzenesulfonyl)amino]-2,3-diydrobenzofurans (6). With neutral propenylbenzenes, either the dihydrobenzofurans, bicyclo[3.2.1]octenediones 17, or products of tandem cycloaddition (79) are formed depending upon reaction conditions. In the latter, molecules with seven to eight asymmetric centers are formed in a single reaction from achiral starting materials. Thus, these seemingly simple reactions yield products of remarkable complexity, and with a high degree of stereoselectivity.