Studies in stereoselective [2+2]-cycloadditions with dichloroketene |
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Authors: | David I MaGee Tammy C Mallais George M Strunz |
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Institution: | a Department of Chemistry, University of New Brunswick, PO Box 45222, Fredericton, NB, Canada E3B 6E2 b Canadian Forestry Service-Atlantic Forestry Centre, Natural Resources Canada, PO Box 4000, Fredericton, NB, Canada E3B 5P7 |
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Abstract: | During the investigation of the reaction of dichloroketene with cyclic enoxy-lactones and acyclic enoxy-ester substrates it was found that only the acylic variants effectively participated in the 2+2]-cycloaddition. Although a complete understanding of the reasons for this are lacking, molecular mechanics calculations do suggest that an out of plane twist of the cabonyl group in the acyclic compounds may be partially responsible. After screening a variety of chiral auxiliaries it was found that useful levels of diastereoselectivity (2.6-10.8:1) could be obtained in this cycloaddition reaction when (R)-2,2-diphenylcyclopentanol was used as the chiral auxiliary. |
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Keywords: | [2+2]-Cycloaddition Diastereoselective Chiral auxiliaries Dioxolanones |
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