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Paper | Special issue | Vol 101, No. 1, 2020, pp.127-144
Published online, 10th April, 2019
DOI: 10.3987/COM-19-S(F)3
Planar Chiral Phosphino[2.2]paracyclophanol-Catalyzed Highly Regio- and Stereoselective [3+2] Annulation Reaction of Morita–Baylis–Hillman Carbonates with Dicyanomethylideneoxindoles

Shinji Kitagaki,* Mayuka Tsuji, Hideki Teramoto, Naoko Takenaga, and Keisuke Yoshida

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan


To demonstrate the utility of [2.2]paracyclophane as a chiral organocatalyst backbone, we examined a planar chiral pseudo-ortho-diarylphosphino[2.2]paracyclophanol, phosphino-PCP-ol, which has a spacer aryl group between the pseudo-ortho-substituted PCP-ol backbone and the diarylphosphino group. We tested this catalyst in the [3+2] annulation reaction of MoritaBaylisHillman carbonates, derived from aromatic aldehydes and methyl acrylate, with 3-(dicyanomethylidene)-2-oxindole. The catalyst produced the desired 3-spirocyclopentene-2-oxindoles in high yields, and high regio-, diastereo-, and enantioselectivities.