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

被引：41

作者：

Tanaka, Takafumi ^{[1
]}

Tanaka, Tsukushi ^{[1
]}

Tsuji, Taro ^{[1
]}

Yazaki, Ryo ^{[1
]}

Ohshima, Takashi ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 8128582, Japan

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 12期

关键词：

BOND-DISSOCIATION ENERGIES; C-H BONDS; OXIDATION; METAL; DIMERIZATION; ACTIVATION; ACIDITIES; KETONE; ROUTE; ACYLPYRAZOLES;

D O I：

10.1021/acs.orglett.8b01313

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 alpha,alpha-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis.

引用

页码：3541 / 3544

页数：4

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