63674-19-1Relevant articles and documents
Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement
Zhang, Liang,Lovinger, Gabriel J.,Edelstein, Emma K.,Szymaniak, Adam A.,Chierchia, Matteo P.,Morken, James P.
, p. 70 - 74 (2016/01/09)
Transition metal catalysis plays a central role in contemporary organic synthesis. Considering the tremendously broad array of transition metal-catalyzed transformations, it is remarkable that the underlying elementary reaction steps are relatively few in
Chiral Mitsunobu reactions with (1S)-(+)-ketopinic acid: Kinetic resolutions of secondary alcohols
Chandrasekhar, Sosale,Kulkarni, Guruprasad
, p. 615 - 619 (2007/10/03)
Several secondary alcohols undergo the Mitsunobu reaction with triphenylphosphine, diethyl azodicarboxylate and (1S)-(+)-ketopinic acid (0.5 equiv. each relative to alcohol) in CH2Cl2 solution at -23°C, to furnish the chiral secondar
Stereochemistry of Aliphatic Carbocations, 15. Rearrangements in 2-Arylalkyl Systems
Kirmse, Wolfgang,Guenther, Bernd-Rainer,Loosen, Karin
, p. 2140 - 2153 (2007/10/02)
Phenyl shifts from secondary to primary carbon proceed with virtually complete inversion at the migration origin, regardless whether they are induced by solvolysis of the aryl sulfonate 25 or by deamination of the amines 12, 17, 26, and 43.Sequential rearrangements (Ph, CH3 and Ph, H) are likewise stereo- and regiospecific.These results strongly support the intervention of phenonium ions.In contrast, the competitive alkyl shifts (deamination only) from benzylic to primary carbon produce but a small excess of inversion (Me 27percent, Et 13percent, iPr 20percent, tBu 3percent).Obviously, benzyl cations are the predominant intermediates.