Nickel-Catalyzed Construction of Chiral 1-[6]Helicenols and Application in the Synthesis of [6]Helicene-Based Phosphinite Ligands

被引：35

作者：

Tsujihara, Tetsuya ^{[1
]}

Inada-Nozaki, Nao ^{[1
]}

Takehara, Tsunayoshi ^{[2
]}

Zhou, Da-Yang ^{[2
]}

Suzuki, Takeyuki ^{[2
]}

Kawano, Tomikazu ^{[1
]}

机构：

[1] Iwate Med Univ, Sch Pharm, Dept Med & Organ Chem, Yahaba, Iwate 0283694, Japan

[2] Osaka Univ, Inst Sci & Ind Res, Osaka 5670047, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 29期

关键词：

Asymmetric catalysis; Cycloaddition; Helical structures; Nickel; P ligands; ASYMMETRIC ALLYLIC ALKYLATION; ENANTIOSELECTIVE GOLD CATALYSIS; 2+2+2 CYCLOADDITION; HELICENE; CYCLOISOMERIZATION; 2-HYDROXYHEXAHELICENE; CARBOHELICENES; HEXAHELICENE; RACEMIZATION; DERIVATIVES;

D O I：

10.1002/ejoc.201600677

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two 1-[6]helicenol derivatives were synthesized by Ni-catalyzed [2+2+2] cycloaddition on a multigram scale. Both enantiomers of the 1-[6]helicenols could be efficiently prepared by simple optical resolution. As a synthetic application of helically chiral 1-[6]helicenols, a novel class of [6]helicene-based phosphinites was developed; these compounds represent the first examples of helically chiral phosphinite ligands. Up to 90 % ee was obtained for the Pd-catalyzed asymmetric allylic alkylation reaction.

引用

页码：4948 / 4952

页数：5

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