Stereoselective synthesis of N,N-acetals by cyclization of an N-acyliminium ion through interaction with an N-sulfonyl group |
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Authors: | Shinji Yamada Yasuko Takahashi |
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Institution: | Department of Chemistry, Ochanomizu University, Bunkyo-ku, Tokyo 112-8610, Japan |
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Abstract: | A new method for the stereoselective synthesis of five- and six-membered bicyclic N,N-acetals with trans configuration was developed using N-acyliminium ion cyclization. The N-sulfonyl substituted compounds were effectively cyclized to give the corresponding acetals in high yields and stereoselectivities, suggesting that the intramolecular interaction between the iminium and the sulfonyl group plays a key role in the cyclization. |
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