Abstract
Abstract The reaction of 1,4-diacetoxy- cis -2-butene 2a with 2-(benzylamino)phenol 3 in THF in the presence of Et 3 N and a catalytic amount of Pd(0)-BHMP-β-Ala 1c gave optically active 4-benzyl-2-vinylbenzoxazine of up to 56.2%ee. The reaction of ( Z )-2-butene-1,4-diylbis(methylcarbonate) 2b instead of 2a with 2-(benzylamino)phenol 3, 4 was obtained with e.e. up to 71.4%. We could improve the enantioselectivity of (R)- 4 by introducing a carboxyl group at the terminal position of the pendant side chain on the bisphosphine ligand and by using a methyl carbonate ester 2b instead of diacetate 2a .
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