Strategy for Catalytic Chemoselective Cross-Enolate Coupling Reaction via a Transient Homocoupling Dimer

Takafumi Tanaka; Tsukushi Tanaka; Taro Tsuji; Ryo Yazaki; Takashi Ohshima

doi:10.1021/acs.orglett.8b01313

Strategy for Catalytic Chemoselective Cross-Enolate Coupling Reaction via a Transient Homocoupling Dimer

Takafumi Tanaka, Tsukushi Tanaka, Taro Tsuji, Ryo Yazaki, Takashi Ohshima

Chemo-Pharmaceutical Sciences

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

15 Citations (Scopus)

Abstract

A new strategy, a transient homocoupling dimer strategy, for direct catalytic oxidative cross-enolate coupling reactions is developed. Cross-enolate coupling products bearing a (contiguous) tetrasubstituted carbon center were obtained chemoselectively without the need for stoichiometric amounts of strong bases/metal oxidants, and thus, the present catalysis provides a general method for the synthesis of unnatural α,α-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis.

Original language	English
Pages (from-to)	3541-3544
Number of pages	4
Journal	Organic letters
Volume	20
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.8b01313
Publication status	Published - Jun 15 2018

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A new strategy, a transient homocoupling dimer strategy, for direct catalytic oxidative cross-enolate coupling reactions is developed. Cross-enolate coupling products bearing a (contiguous) tetrasubstituted carbon center were obtained chemoselectively without the need for stoichiometric amounts of strong bases/metal oxidants, and thus, the present catalysis provides a general method for the synthesis of unnatural α,α-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis.",

author = "Takafumi Tanaka and Tsukushi Tanaka and Taro Tsuji and Ryo Yazaki and Takashi Ohshima",

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T1 - Strategy for Catalytic Chemoselective Cross-Enolate Coupling Reaction via a Transient Homocoupling Dimer

AU - Tanaka, Takafumi

AU - Tanaka, Tsukushi

AU - Tsuji, Taro

AU - Yazaki, Ryo

AU - Ohshima, Takashi

PY - 2018/6/15

Y1 - 2018/6/15

N2 - A new strategy, a transient homocoupling dimer strategy, for direct catalytic oxidative cross-enolate coupling reactions is developed. Cross-enolate coupling products bearing a (contiguous) tetrasubstituted carbon center were obtained chemoselectively without the need for stoichiometric amounts of strong bases/metal oxidants, and thus, the present catalysis provides a general method for the synthesis of unnatural α,α-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis.

AB - A new strategy, a transient homocoupling dimer strategy, for direct catalytic oxidative cross-enolate coupling reactions is developed. Cross-enolate coupling products bearing a (contiguous) tetrasubstituted carbon center were obtained chemoselectively without the need for stoichiometric amounts of strong bases/metal oxidants, and thus, the present catalysis provides a general method for the synthesis of unnatural α,α-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis.

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JO - Organic Letters

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