73826-09-2Relevant articles and documents
Catalytic enantioselective dehydrogenative Si-O coupling of oxime ether-functionalized alcohols
Weickgenannt, Andreas,Mohr, Jens,Oestreich, Martin
, p. 3468 - 3479 (2012/06/18)
Asymmetric silylation of alcohols is an unusual but effective approach to their kinetic resolution, and the Cu-H-catalyzed dehydrogenative Si-O coupling is particularly noteworthy as dihydrogen is formed as the sole by-product. Our laboratory had previously reported on diastereoselective (with silicon-stereogenic silanes) and enantioselective (with achiral silanes) Si-O couplings of azine donor-functionalized alcohols. The limitation, that is, the requirement of a nitrogen donor atom, prompted us to seek equally useful donor groups. Oxime ethers were identified as a suitable alternative, and we describe herein the preparation of a series of oxime ether-functionalized alcohols. To assess different substitution patterns in their kinetic resolution, these were tested in the reagent-controlled Si-O coupling using a silicon-stereogenic silane. The optimal substituents at the oxime carbon atom (dr=85:15 in the diastereoselective coupling) were then chosen for the related catalyst-controlled Si-O coupling but selectivity factors were only moderate.
Aqueous-mediated ring opening of epoxides with oximes: A rapid entry into β-hydroxy oxime O-ethers as potential β-adrenergic blocking agents
Rad, Mohammad Navid Soltani,Behrouz, Somayeh,Dianat, Manije
experimental part, p. 2055 - 2064 (2009/04/03)
Novel β-hydroxy oxime O-ethers, as potential β-adrener-gic blocking agents, were synthesized from the aqueous-mediated (H2O - DMSO, 7:3) O-alkylation of oximes with epoxides in the presence of potassium hydroxide at room temperature. The O-alkylation was regioselective and (E)-oxime ethers were the main products. The results of quantum mechanical studies used to rationalize the experimental outcomes are discussed. Thieme Stuttgart.
