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Communication | Special issue | Vol 103, No. 2, 2021, pp.678-686
Published online, 5th February, 2021
DOI: 10.3987/COM-20-S(K)58
Planar Chiral [2.2]Paracyclophane-Based Bis(thiourea)-Catalyzed Highly Diastereo- and Enantioselective Michael Addition Reaction of Nitroethane to Nitrostyrenes

Shinji Kitagaki,* Eriko Shimo, Sawa Takeda, Rintaro Fukai, Naohiro Kojima, Shun Yoshioka, Naoko Takenaga, and Keisuke Yoshida

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

Abstract

To demonstrate the utility of [2.2]paracyclophane as a chiral organocatalyst backbone, we evaluated a planar chiral pseudo-ortho- [2.2]paracyclophane-based bis(thiourea) catalyst in the Michael addition reaction of nitroethane to nitrostyrenes. The catalyst produced the desired 1,3-dinitro compounds in high yields and high diastereo- and enantioselectivities.