17668-60-9Relevant articles and documents
Epoxysilanes as substrates in regio- and stereo-specific synthesis of silylated γ-hydroxyphosphane oxides, precursors of stereodefined allylphosphane oxides
González-Nogal, Ana M.,Cuadrado, Purificación
, p. 8080 - 8087 (2013/08/23)
Epoxysilanes experienced trans stereospecific α- or β-cleavage by the lithium derivative of methyldiphenylphosphane oxide leading to different compounds. The behaviour of the epoxysilanes towards this nucleophilic reagent depends on the nature of the sily
Asymmetric dihydroxylation of allylic phosphine oxides
Nelson, Adam,Warren, Stuart
, p. 2645 - 2657 (2007/10/03)
Diphenylphosphinoyl diols have been produced by asymmetric dihydroxylation (AD) of allylic phosphine oxides and have been shown to be useful synthetic intermediates. The results of this study are discussed in terms of the model which has been proposed by Sharpless to explain the enantioselectivity of his AD reaction. The dihydroxylation results are thus of both mechanistic and synthetic value.
Asymmetric dihydroxylations of allylic phosphine oxides
Nelson,O'Brien,Warren
, p. 2685 - 2688 (2007/10/02)
Allylic phosphine oxides 6 undergo asymmetric dihydroxylation to yield 1,2 diols 9. The enantioselectivity of these reactions depends critically on the class and quantity of chiral ligand used. A model to explain the sense and degree of asymmetric inducti
An Unusual Stereochemical Directing Effect of Propargylic Oxygen Substituents on an Intramolecular Diels-Alder Reaction
Trost, Barry M.,Holcomb, Ryan C.
, p. 7157 - 7160 (2007/10/02)
Varying the substituent on the oxygen of a propargylic alcohol affects the stereochemical course of an intramolecular Diels-Alder reaction of a diene-yne.
Aprotic Conjugate Addition of Allyllithium Reagents Bearing Polar Groups to Cyclic Enones. 1. 3-Alkylallyl Systems
Binns, Malcolm R.,Haynes, Richard K.,Katsifis, Andrew G.,Schober, Paul A.,Vonwiller, Simone C.
, p. 5411 - 5423 (2007/10/02)
The conjugate addition of lithiated (E)- and (Z)-oct-2-enyl sulfoxides and phosphine oxides, but-2-enyl sulfoxides, phosphine oxides and phosphonates, and 3,3-dimethylallyl and allyl sulfoxides to cyclic enones has been examined.The E and Z carbanions react in highly diastereoselective fashion with five-membered cyclic enones to deliver respectively syn and anti vinylic sulfoxides, phosphine oxides, and phosphonates.Hexamethylphosphoric triamide has no regiochemical influence on these reactions.The regiochemical and stereochemical outcomes of these reactions are rationalized in terms of planar lithiated reagents in which Li+ is bound to oxygen attached to sulfur or phosphorus of the polar group and a 10-membered "trans-decalyl"- or "trans-fused chair-chair"-like transition-state model in which the lithiated reagent adopts an endo orientation over one face of the enone such that for the reagent, the 3-alkyl group is pseudoequatorial, and for the Z, pseudoaxial.
Phosphinyl-Substituted Dienophiles: Their Synthesis and Directive Effects
Darling, Stephen D.,Brandes, Stephanie J.
, p. 1413 - 1416 (2007/10/02)
The unilateral directive influence of the carbonyl group in the Diels-Alder reaction can be negated by a diphenylphosphinyl group.The dienophile 4-(diphenylphosphinyl)-3-buten-2-one (4) was synthesized.Products isolated as a result of the addition of 4 to