Asymmetric Organocatalytic Sequential Reaction of Structurally Complex Cyclic Hemiacetals and Functionalized
Jun-Ping Pei1, Ying-Han Chen1, Yan-Kai Liu1,2
1Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy , Ocean University of China , Qingdao 266003 , People's Republic of China.
Abstract:
Structurally complex cyclic hemiacetals bearing a racemic tetrasubstituted stereocenter have been prepared in a concise manner and were successfully used in an organocatalytic enantioselective sequence to react with functionalized nitro-olefins, providing bicyclic acetal-containing compounds as two separable epimers with excellent stereoselectivity. The reaction showed broad substrate scope, with respect to the starting hemiacetals. Moreover, this protocol allows the synthetic transformation of the products to various interesting heterocyclic compounds with substantial structural diversity and broad functionality.
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