Phenol 3-aryloxy-1-alkene

The oxyamination of ( )-l-deuterio-l-decene was >95% diastereoselective. but not re-gioselective61. Complete regioselectivity was, however, observed on (E)-l-phcnyl-l-propene and 3-aryloxy-l-propene, from which l-(aryloxy)-2-hydroxypropanamides, a class of biologically active substances with -adrenergic receptor blocking effects, were obtained62. Limited reactivity of internal alkenes, especially (Z)-alkenes, was observed. Finally, phenol can be used instead of acetic acid. 

The (l )-(-)-COP-OAc dimer enantiomer [849592-74-1] M 1512.2, m 241-251" dec. is prepared in the same way but using the enantiomeric starting material. [Stevens Richards Organometallics 18 1346 1999, Anderson et al. Org Synth 84 148 2007.] The reactions of trichloroacetimidate derivatives of Z-2-alken-l-ols with phenolic nucleophiles in the presence of chiral COP-OAc dimer catalysts yield 3-aryloxy-l-alkenes in high yield (63-90%) and high enantiomeric purity (90-97% ee) and are compatible with the presence of base-labile substituents in either reactant [Kirsch, Overman and White Org Lett 9 911 2007],... 

---