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- Title
N, N′-Dioxide/Nickel(II)-Catalyzed Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction of β,γ-Unsaturated α-Ketoesters with Enecarbamates.
- Authors
Zhou, Yuhang; Zhu, Yin; Lin, Lili; Zhang, Yulong; Zheng, Jianfeng; Liu, Xiaohua; Feng, Xiaoming
- Abstract
N, N′-Dioxide/nickel(II) complexes have been developed to catalyze the inverse-electron-demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters with acyclic enecarbamates. After detailed screening of the reaction parameters, mild optimized reaction conditions were established, affording 3,4-dihydro-2 H-pyranamines in up to 99 % yield, 99 % ee and more than 95:5 d.r. The catalytic system was also efficient for β-substituted acyclic enecarbamates, affording more challenging 2,3,4-trisubstituted 3,4-dihydro-2 H-pyranamine with three contiguous stereogenic centers in excellent yields, diastereoselectivities, and enantioselectivities. The reaction could be scaled up to a gram scale with no deterioration of either enantioselectivity or yield. Based on these experiments and on previous reports, a possible transition state was proposed.
- Subjects
DIELS-Alder reaction; CHEMICAL reactions; NITROGEN compound synthesis; ESTER derivatives; NUCLEOPHILES
- Publication
Chemistry - A European Journal, 2014, Vol 20, Issue 50, p16753
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201403764