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Published on: February 27, 2017
Catalytic and Enantioselective Synthesis of Inherently Chiral Saddle-Shaped Compounds by [2 + 2 + 2] Cycloaddition of
Takanori Shibata1, Masahiro Nakada1, Kousuke Senda1
1Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo, 169-8555, Japan.
Abstract:
In this paper, we describe a chiral Rh-catalyzed [2 + 2 + 2] cycloaddition of 1,8-naphthylene-based 1,10-diynes of an anti/syn mixture with alkynoates. Thermodynamically stable saddle-shaped chiral cycloadducts were obtained in good-to-high yields and enantiomeric ratios. Hetero [2 + 2 + 2] cycloaddition using aryl cyanides also proceeded to give the corresponding inherently chiral pyridine-containing compounds.
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