154503-33-0Relevant academic research and scientific papers
Silylene oxonium ylides: di-tert-butylsilylene insertion into C-O bonds
Bourque, Laura E.,Haile, Pamela A.,Loy, Janice M.N.,Woerpel
experimental part, p. 5608 - 5613 (2009/12/01)
Allylic ethers undergo insertions of silylenes into C-O bonds to form allylic silanes. Silylene insertion into C-O acetal bonds was also observed. Formation of silylene ylide intermediates led to [1,2]-Stevens rearrangement products as well as [2,3]-sigma
Diastereoselective, three-component cascade synthesis of tetrahydrofurans and tetrahydropyrans employing the tandem Mukaiyama aldol-lactonization process
Mitchell, T. Andrew,Zhao, Cunxiang,Romo, Daniel
supporting information; experimental part, p. 9544 - 9551 (2009/04/07)
(Chemical Equation Presented) 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 γ-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 β-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 δ-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.
Cerium(IV), as a selective and efficient catalyst for alcoholyses of allylic and tertiary benzylic alcohols
Iranpoor, Nasser,Mothaghineghad, Enayatholah
, p. 1859 - 1870 (2007/10/02)
An efficient and selective method is described for the catalytic conversion of allylic, and tertiary benzylic alcohols into their corresponding ethers in the presence of Ce(IV) under solvolytic and non- solvolytic conditions.
