期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 126, 期 27, 页码 8569-8575出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja048301m
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We report three highly stereoselective pericyclic reactions occurring in cascade leading to the synthesis of Decalins skeletons possessing two contiguous quaternary centers. The tandem reaction is triggered by an oxy-Cope rearrangement to create in situ a 10-membered ring enol ether macrocyle 6, which immediately rearranges via a Claisen [3,3] shift to the corresponding E-cyclodec-6-en-1-one 7. The latter spontaneously cyclizes via a transannular ene reaction to produce Decalin 5. Analysis of the mechanism with respect to the origin of the high diastereoselectivity of the tandem oxy-Cope/Claisen/ene reaction is presented.
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