1360054-30-3Relevant articles and documents
Synthesis of desfluorinated nebivolol isomers
Khandavalli, Purushothama Chary,Spiess, Oliver,B?hm, Oliver M.,Freifeld, Ilia,Kesseler, Kurt,Jas, Gerhard,Schinzer, Dieter
, p. 3965 - 3973 (2015/05/12)
The syntheses of all possible stereoisomers of desfluorinated side products of the potent antihypertensive β-blocker nebivolol are reported. A straightforward approach using a common racemic precursor was employed to obtain the desired optically active building blocks. For one series of compounds, a Sharpless asymmetric epoxidation (SAE) route yielded in a direct fashion the required compounds whereas a Mitsunobu reaction was selected to obtain the other series of compounds. This offers a flexible approach to all desfluoronebivolol side-products in order to fully characterize them.
Palladium(II)-catalyzed enantioselective synthesis of 2-vinyl oxygen heterocycles
Cannon, Jeffrey S.,Olson, Angela C.,Overman, Larry E.,Solomon, Nicole S.
supporting information; scheme or table, p. 1961 - 1973 (2012/05/05)
2-Vinylchromanes (1), 2-vinyl-1,4-benzodioxanes (2), and 2,3-dihydro-2-vinyl-2H-1,4-benzoxazines (3) can be prepared in high yields (90-98%) and excellent enantiomeric purities (87-98% ee) by [COP-OAc] 2-catalyzed cyclization of phenolic (E)-allylic trichloroacetimidate precursors. Deuterium-labeling and computational experiments are consistent with these cyclization reactions taking place by an anti-oxypalladation/syn- deoxypalladation mechanism. 2-Vinylchromanes can also be prepared in good yields and high enantiomeric purities from analogous (E)-allylic acetate precursors, which constitutes the first report that acetate is a competent leaving group in COP-catalyzed enantioselective SN2′ substitution reactions.
