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

8 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

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All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Tanaka, T., Tanaka, T., Tsuji, T., Yazaki, R., & Ohshima, T. (2018). Strategy for Catalytic Chemoselective Cross-Enolate Coupling Reaction via a Transient Homocoupling Dimer. Organic letters, 20(12), 3541-3544. https://doi.org/10.1021/acs.orglett.8b01313

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AU - Ohshima, Takashi

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10.1021/acs.orglett.8b01313