Catalytic asymmetric [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides

Kohei Orimoto; Harufumi Oyama; Yuki Namera; Takashi Niwa; Masahisa Nakada

doi:10.1021/ol303381c

Catalytic asymmetric [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides

Kohei Orimoto, Harufumi Oyama, Yuki Namera, Takashi Niwa, Masahisa Nakada

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	768-771
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	4
DOIs	https://doi.org/10.1021/ol303381c
Publication status	Published - 2013 Feb 15

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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T1 - Catalytic asymmetric [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides

AU - Orimoto, Kohei

AU - Oyama, Harufumi

AU - Namera, Yuki

AU - Niwa, Takashi

AU - Nakada, Masahisa

PY - 2013/2/15

Y1 - 2013/2/15

N2 - 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.

AB - 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.

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Catalytic asymmetric [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides

Abstract

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