A convenient route to enantiomerically pure highly oxygenated decalins from sugar allyltin derivatives |
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| Institution: | 1. Department of Chemistry, Renmin University of China, Beijing 100872, China;2. State Key Laboratory of Heavy Oil Processing, China University of Petroleum, Beijing 102249, China;1. School of Architecture and Urban-Rural Planning, Fuzhou University, Fuzhou 350108, China;2. Institute of Geography, Ruhr University Bochum, Bochum 44801, Germany;1. School of Food Science and Technology, Dalian Polytechnic University, Dalian, Liaoning, 116034, People''s Republic of China;2. National Engineering Research Center of Seafood, Dalian, Liaoning, 116034, People''s Republic of China;3. Engineering Research Center of Seafood of Ministry of Education of China, Dalian, Liaoning, 116034, People''s Republic of China |
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| Abstract: | Preparation of enantiomerically pure, highly oxygenated decalins via tandem Wittig-type Diels–Alder reactions from the corresponding sugar-derived dieno-phosphoranes and/or -phosphonates and sugar aldehydes is described. Application of the phosphonates is more convenient than phosphoranes since the former can be prepared in much higher yields and react with aldehydes under milder conditions. The intermediate trienes resulting from the Wittig-type process undergo spontaneous and highly stereoselective cyclization to the cis-decalins under the reaction conditions. |
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