TY - JOUR
T1 - Chirality transfer in palladium catalyzed reactions of allylammonium salts
AU - Doi, Takayuki
AU - Yanagisawa, Arata
AU - Miyazawa, Masahiro
AU - Yamamoto, Keiji
N1 - Funding Information:
ACKNOWLEDGMENT. Support by the Grant-in-Aid for Genenal Scientific Research (No. 0440301) from the Ministry of Education, Science, and Culture is gratefully acknowledged.
PY - 1995/2
Y1 - 1995/2
N2 - Optically active 1-isobutyl-2(Z)-butenyltrimethylammonium iodide (10) underwent allylation with dimethyl sodiomalonate in the presence of a palladium(0) catalyst. The reaction proceeded predominantly with 1,3 transposition and with inversion of configuration due probably to a prior isomerization from anti to syn-π-allylpalladium intermediate (14→15). The stereochemistry observed in the reaction with phenylzinc chloride was opposite to that with the soft nucleophile.
AB - Optically active 1-isobutyl-2(Z)-butenyltrimethylammonium iodide (10) underwent allylation with dimethyl sodiomalonate in the presence of a palladium(0) catalyst. The reaction proceeded predominantly with 1,3 transposition and with inversion of configuration due probably to a prior isomerization from anti to syn-π-allylpalladium intermediate (14→15). The stereochemistry observed in the reaction with phenylzinc chloride was opposite to that with the soft nucleophile.
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U2 - 10.1016/0957-4166(95)00021-G
DO - 10.1016/0957-4166(95)00021-G
M3 - Article
AN - SCOPUS:0028921695
SN - 0957-4166
VL - 6
SP - 389
EP - 392
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 2
ER -