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Palladium-catalyzed asymmetric tandem allylic substitution using chiral 2-(phosphinophenyl)pyridine ligand |
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| Authors: | Katsuji Ito Yoshikatsu Imahayashi Shuuichiro Eno Tsutomu Katsuki |
| Affiliation: | a Department of Chemistry, Fukuoka University of Education, Akama, Munakata, Fukuoka 811-4192, Japan b Department of Chemistry, Faculty of Science, Graduate School, Kyushu University 33, 6-10-1 Hakozaki, Highosi-ku, Fukuoka 812-8581, Japan c CREST, Japan Science and Technology Agency (JST), Japan |
| Abstract: | Palladium-catalyzed asymmetric tandem allylic substitution of (Z)-1,4-diacyloxy- and (Z)-1,4-bis(alkoxycarbonyloxy)-2-butene (2a-c) using 2-(phosphinophenyl)pyridine 1 as chiral ligand provided optically active six-membered 2-vinyl-1,4-diheterocyclic compounds with good to high enantioselectivity. For example, the reactions with catechol, 2-(benzylamino)phenol, or 1,2-bis(benzylamino)ethane as a nucleophile gave 2-vinyl-1,4-benzodioxane (71% ee), 4-benzyl-2-vinyl-1,4-benzoxazine (86% ee), and 1,4-dibenzyl-2-vinylpiperazine (86% ee), respectively. |
| Keywords: | Palladium Asymmetric catalysis P,N ligand Tandem allylic substitution |
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