Tetrahedron

2, 2′-Isopropylidenebis [(4S, 5R)-4, 5-di (2-naphthyl)-2-oxazoline] ligand for asymmetric cyclization–carbonylation of meso-2-alkyl-2-propargylcyclohexane-1, 3-diols

…, C Matsuba, T Kusakabe, H Takayama, S Yamamura…

Index: Kato, Keisuke; Matsuba, Chie; Kusakabe, Taichi; Takayama, Hiroyuki; Yamamura, Shigeo; Mochida, Tomoyuki; Akita, Hiroyuki; Peganova, Tat'yana A.; Vologdin, Nikolai V.; Gusev, Oleg V. Tetrahedron, 2006 , vol. 62, # 42 p. 9988 - 9999

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Citation Number: 27

Abstract

The oxidative cyclization–carbonylation of meso-2-alkyl-2-propargylcyclohexane-1, 3-diols mediated by Pd (II) with chiral bisoxazoline (box ligand) afforded bicyclic-β-alkoxyacrylates. Based on a ligand screening, 2, 2′-isopropylidenebis [(4S, 5R)-4, 5-di (2-naphthyl)-2- oxazoline] ligand has been developed. The products with a chiral quaternary carbon were obtained in 71–100% yields with 85–95% ee.