The diastereoselective hydrochlorination of α,β-unsaturated chiral imides by reaction with BCl2OR or BCl(OR)2 type reagents is described. Complete diastereoselectivity is achieved through the use of new oxazolidin-2-ones ad hoc prepared for this purpose from (S)-tryptophan. An hypothesis on the donor-acceptor interactions, between the substrate and the Lewis acids, that drive the attack of the chloride preferentially to one face of the alkenoyl chain is reported. © 1995.
Cardillo G., Di Martino E., Gentilucci L., Tomasini C., Tomasoni L. (1995). Conjugate addition of chloride to α,β-unsaturated chiral imides promoted by BCl3-derivatives. Part II. TETRAHEDRON-ASYMMETRY, 6(8), 1957-1963 [10.1016/0957-4166(95)00255-N].
Conjugate addition of chloride to α,β-unsaturated chiral imides promoted by BCl3-derivatives. Part II
Gentilucci L.;Tomasini C.;Tomasoni L.
1995
Abstract
The diastereoselective hydrochlorination of α,β-unsaturated chiral imides by reaction with BCl2OR or BCl(OR)2 type reagents is described. Complete diastereoselectivity is achieved through the use of new oxazolidin-2-ones ad hoc prepared for this purpose from (S)-tryptophan. An hypothesis on the donor-acceptor interactions, between the substrate and the Lewis acids, that drive the attack of the chloride preferentially to one face of the alkenoyl chain is reported. © 1995.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
