54656-65-4Relevant articles and documents
Conformational Study of Chiral Alkenes: The Influence of Protective Groups on the Relative Stability of Ground-State Rotational Isomers
Gung, Benjamin W.,Wolf, Mark A.
, p. 7038 - 7044 (1993)
A variable temperature NMR study shows that a protective group on the hydroxy function of a chiral allylic alcohol can either enhance or counter the influence of the vinyl substituent on the ground-state (GS) conformations.If the allylic hydroxy is protected as a methyl ether, the CH-eclipsed form I becomes favored to a greater degree for normal chiral alkenes.Furthermore, conformer I becomes preferred even for the γ-hydroxy-α,β-unsaturated esters, which normally favor the CO-eclipsed form (II).On the other hand, the tert-butyldimethylsilyl (TBDMS) ether enhances the preference for conformer II for the γ-hydroxy-α,β-unsaturated esters and diminishes the preference for the CH-eclipsed form of normal chiral alkenes.These facts are explained by the size of the allylic oxygen lone pairs.
Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents
Malmedy, Florence,Wirth, Thomas
supporting information, p. 16072 - 16077 (2016/10/30)
The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.
Ether-directed diastereoselectivity in catalysed Overman rearrangement: comparative studies of metal catalysts
Jaunzeme, Ieva,Jirgensons, Aigars
, p. 5794 - 5799 (2008/09/21)
Ether-directed diastereoselectivity in Overman rearrangement of δ-methoxy and δ-TBDMSO substituted allylic trichloroacetimidates has been explored using PtCl2, PtCl4, AuCl and AuCl3 catalysts in comparison with commonly us
