6244-60-6Relevant academic research and scientific papers
O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols
Jeffrey, Jenna L.,Terrett, Jack A.,MacMillant, David W.C.
, p. 1532 - 1536 (2015/10/05)
The efficiency and selectivity of hydrogen atom transfer from organic molecules are often difficult to control in the presence of multiple potential hydrogen atom donors and acceptors. Here, we describe the mechanistic evaluation of a mode of catalytic activation that accomplishes the highly selective photoredox a-alkylation/lactonization of alcohols with methyl acrylate via a hydrogen atom transfer mechanism. Our studies indicate a particular role of tetra-n-butylammonium phosphate in enhancing the selectivity for α C-H bonds in alcohols in the presence of allylic, benzylic, α-C=O, and α-ether C-H bonds.
Enantioselective synthesis of syn / anti -1,3-amino alcohols via proline-catalyzed sequential α-aminoxylation/α-amination and horner-wadsworth-emmons olefination of aldehydes
Jha, Vishwajeet,Kondekar, Nagendra B.,Kumar, Pradeep
supporting information; experimental part, p. 2762 - 2765 (2010/08/19)
(Figure presented) A novel and general method for asymmetric synthesis of both syn/anti-1,3-amino alcohols is described. The method uses proline-catalyzed sequential α-aminoxylation/ α-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step. By using this method, a short synthesis of a bioactive molecule, (R)-1-((S)-1-methylpyrrolidin-2-yl)-5- phenylpentan-2-ol, is also accomplished.
Stereoselective C-glycosylation reactions of ribose derivatives: Electronic effects of five-membered ring oxocarbenium ions
Larsen, Catharine H.,Ridgway, Brian H.,Shaw, Jared T.,Smith, Deborah M.,Woerpel
, p. 10879 - 10884 (2007/10/03)
The factors controlling the highly α-selective C-glycosylation of ribose derivatives were determined by examining the Stereoselective reactions of 18 ribose analogues differing in substitution at C-2, C-3, and C-4. The lowest energy conformers of the intermediate oxocarbenium ions display the C-3 alkoxy group in a pseudoaxial orientation to maximize electrostatic effects. To a lesser extent, the C-2 substituent prefers a pseudoequatorial position, and the alkyl group at C-4 has little influence on conformational preferences. In all cases, the product was formed by stereoelectronically preferred inside attack on the lowest energy conformer.
