Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system

Hiroyuki Suga; Masahiro Yoshiwara; Takaaki Yamaguchi; Takashi Bando; Mizuki Taguchi; Ayano Inaba; Yuichi Goto; Ayaka Kikuchi; Kennosuke Itoh; Yasunori Toda

doi:10.1039/C8CC09224A

Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system†

Hiroyuki Suga,

*^a Masahiro Yoshiwara,^a Takaaki Yamaguchi,^a Takashi Bando,^a Mizuki Taguchi,^a Ayano Inaba,^a Yuichi Goto,^a Ayaka Kikuchi,^a Kennosuke Itoh

^bc and Yasunori Toda

^a

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* Corresponding authors

^a Department of Materials Chemistry, Faculty of Engineering, Shinshu University, Wakasato, Nagano 380-8553, Japan

^b Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan

^c Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan

Abstract

The first example of asymmetric 1,3-dipolar cycloadditions between diazo imine-derived cyclic azomethine ylides and acryloylpyrazolidinone using a rhodium(II) complex/chiral Lewis acid binary system is reported. The asymmetric cycloadditions afforded optically active 8-oxabicyclo[3.2.1]octanes with high diastereo- and enantioselectivities (up to >99 : 1 dr, 99% ee). A switch of exo/endo-selectivity was observed depending on the diazo substrates.

Chemical Communications

Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system†

Abstract

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Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system

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