Tetrahedron: Asymmetry

C 2-Symmetric bicyclo [3.3. 1] nona-2, 6-diene and bicyclo [3.3. 2] deca-2, 6-diene: new chiral diene ligands based on the 1, 5-cyclooctadiene framework

Y Otomaru, A Kina, R Shintani, T Hayashi

Index: Otomaru, Yusuke; Kina, Asato; Shintani, Ryo; Hayashi, Tamio Tetrahedron Asymmetry, 2005 , vol. 16, # 9 p. 1673 - 1679

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Citation Number: 96

Abstract

As a new type of C2-symmetric chiral diene ligands, which coordinate to a metal by their 1, 5- cyclooctadiene framework, we prepared 2, 6-disubstituted bicyclo [3.3. 1] nona-2, 6-diene (bnd*) and bicyclo [3.3. 2] deca-2, 6-diene (bdd*), and examined their catalytic activity and enantioselectivity for rhodium-catalyzed asymmetric 1, 4-addition to α, β-unsaturated ketones and 1, 2-addition to N-sulfonylimines. High enantioselectivity of the Ph-bnd* ...