TY - JOUR
T1 - Enantioselective elimination reaction of a 6,6-membered bicyclic allylic carbonate. Importance of chirality reversal depending on the palladium-chiral phosphine ratio
AU - Shimizu, Isao
AU - Matsumoto, Yoshiyuki
AU - Shoji, Ken
AU - Ono, Toshiya
AU - Satake, Akiharu
AU - Yamamoto, Akio
PY - 1996/9/23
Y1 - 1996/9/23
N2 - Reaction of (±)-8α-methoxycarbonyloxy-4αβ-methyl-2,3,4,4a,5,6,7,8-octahydronap hthalene (1) in the presence of a palladium-chiral phosphine catalyst gave 4a-methyl-3,4,4a,5,6,7-hexahydronaphthalene (2) enantioselectively. When the reaction was carried out using Pd(OAc)2 and (S)-(-)-BINAP, the enantioselection was influenced by the phosphine to palladium ratio, because (S)-BINAP oxide generated in situ acted as a ligand causing the opposite enantioselectivity. High enantioselectivity (86% ee) was obtained when (1-Me-C3H5-PdCl)2 and (S)-(-)-p-Tol-BINAP were used.
AB - Reaction of (±)-8α-methoxycarbonyloxy-4αβ-methyl-2,3,4,4a,5,6,7,8-octahydronap hthalene (1) in the presence of a palladium-chiral phosphine catalyst gave 4a-methyl-3,4,4a,5,6,7-hexahydronaphthalene (2) enantioselectively. When the reaction was carried out using Pd(OAc)2 and (S)-(-)-BINAP, the enantioselection was influenced by the phosphine to palladium ratio, because (S)-BINAP oxide generated in situ acted as a ligand causing the opposite enantioselectivity. High enantioselectivity (86% ee) was obtained when (1-Me-C3H5-PdCl)2 and (S)-(-)-p-Tol-BINAP were used.
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U2 - 10.1016/0040-4039(96)01587-0
DO - 10.1016/0040-4039(96)01587-0
M3 - Article
AN - SCOPUS:0030599224
SN - 0040-4039
VL - 37
SP - 7115
EP - 7118
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 39
ER -