74262-58-1Relevant academic research and scientific papers
Metal-catalyzed silylene insertions of allylic ethers: Stereoselective formation of chiral allylic silanes
Bourque, Laura E.,Cleary, Pamela A.,Woerpel
, p. 12602 - 12603 (2008/09/16)
Silylene insertion into allylic ethers occurs suprafacially to provide enantioenriched allylic silanes and disilanes. Silylene insertion to a variety of protected allylic alcohols utilizing silver- and copper-mediated conditions proved to be a general method for allylic silane formation. Allylic disilanes reacted similarly to allylic silanes, undergoing both annulation and allylation reactions. Copyright
Olivanic Acid Analogues. Part 2. Total Synthesis of Some C(6)-Substituted 7-Oxo-1-azabicyclohept-2-ene-2-carboxylates
Bateson, John H.,Quinn, Alison M.,Smale, Terence C.,Southgate, Robert
, p. 2219 - 2234 (2007/10/02)
A number of 6-substituted 7-oxo-1-azabicyclohept-2-ene-2-carboxylates related to the olivanic acids were prepared from the phosphorane (32).Generation of the anion α to the azetidin-2-one carbonyl group, followed by reaction with electrophiles and intramolecular cyclisation using the Wittig procedure gave the bicyclic products; in all cases the thermodynamically favoured trans-stereochemisty about the azetidinone ring predominated.In contrast, some less readily available cis-substituted analogues were obtained from the cyclohexa-1,4-diene derived phosphorane (61).The synthetic utility of a masked acetonyl ester group for preparing the free acids of these azabicycloheptene ring systems is described.
Acyclic Stereoselection. 9. Stereochemistry of the Addition of Lithium Enolates to α-Alkoxy Aldehydes
Heathcock, Clayton H.,Young, Steven D.,Hagen, James P.,Pirrung, Michael C.,White, Charles T.,VanDerveer, Don
, p. 3846 - 3856 (2007/10/02)
The stereochemistry of addition of lithium enolates derived from esters and ketones to the α-alkoxy aldehydes 1-5 has been investigated.In all cases, the predominant product is that predicted by application of Felkin's model for asymmetric induction and by assuming the alkoxy group to be the "large" group.The Cram cyclic model for asymmetric induction is not followed.Stereostructures have been assigned by a combination of conversion to products of known stereostructure, 13C and 1H NMR correlations, and single-crystal X-ray analysis.
