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Catalytic Asymmetric [4 + 2] Cycloadditions and Hosomi–Sakurai Reactions of α‑Alkylidene β‑Keto Imides

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posted on 15.02.2013, 00:00 by Kohei Orimoto, Harufumi Oyama, Yuki Namera, Takashi Niwa, Masahisa Nakada
Highly enantioselective catalytic asymmetric reactions of rationally designed α-alkylidene β-keto imides are described. The [4 + 2] cycloadditions and Hosomi–Sakurai reactions of α-alkylidene β-keto imides proceed with high enantioselectivity and yield. The [4 + 2] cycloadditions of the imides with various dienes afford products bearing an all-carbon quaternary stereogenic center at the ring junction. α-Alkylidene β-keto imides should be useful for the enantioselective total synthesis of natural products and other catalytic asymmetric applications.