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• W2052182417 endingPage "9551" @default.
• W2052182417 startingPage "9544" @default.
• W2052182417 abstract "A full account of studies leading to the development of a cascade sequence that generates as many as two C-C bonds, one C-O bond, and three new stereocenters providing substituted tetrahydrofurans (THFs) from simple gamma-ketoaldehydes and thiopyridyl ketene acetals is described. The process involves a tandem Mukaiyama aldol-lactonization (TMAL) and accumulated evidence suggests the intermediacy of a silylated beta-lactone that is intercepted by the pendant ketone. Formation of a cyclic oxocarbenium is followed by reduction with silicon-based nucleophiles leading to a highly diastereoselective synthesis of tetrahydrofurans. This cascade process has now been extended to the synthesis of tetrahydropyrans from simple delta-ketoaldehydes. The stereochemical outcome of the cascade processes described was determined by NOE correlations, coupling constant analysis, and X-ray crystallography of the derived oxygen heterocycles and is in accord with established and recently proposed models for nucleophilic additions to cyclic 5- and 6-membered oxocarbenium ions. The utility of this process was demonstrated by the synthesis of the tetrahydrofuran fragment of colopsinol B." @default.
• W2052182417 created "2016-06-24" @default.
• W2052182417 creator A5011880323 @default.
• W2052182417 creator A5029986655 @default.
• W2052182417 creator A5091108204 @default.
• W2052182417 date "2008-11-16" @default.
• W2052182417 modified "2023-09-23" @default.
• W2052182417 title "Diastereoselective, Three-Component Cascade Synthesis of Tetrahydrofurans and Tetrahydropyrans Employing the Tandem Mukaiyama Aldol−Lactonization Process" @default.
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