Modified synthesis of heptahelicene and its resolution into single enantiomers

被引：15

作者：

Alexandrova, Zuzana

Sehnal, Petr

Stara, Irena G.

Stary, Ivo

Saman, David

Urquhart, Stephen G.

Otero, Edwige

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Ctr Biomol & Complex Mol Syst, CR-16610 Prague 6, Czech Republic

[2] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2006年 / 71卷 / 08期

关键词：

helicenes; heptahelicene; alkynes; triynes; cycliosomerization; cobalt catalysis; nickel catalysis; enantioselective catalysis; racemate resolution; chiral HPLC;

D O I：

10.1135/cccc20061256

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A practical synthesis of racemic heptahelicene has been develeped being based on key [2+ 2+ 2] cycloisomerization of bis[2-(but-3-yn-1-yl)-1-naphthyl] acetylene under CpCo(CO)(2)/ PPh3 or CpCo(C2H4)(2) catalysis. The application of the Ni(cod)(2) catalyst with (-)-(S-a)-(2'-methoxy-1,1'-binaphthalen-2-yl) diphenylphosphane resulted in enantioselective triyne cyclization to provide (+)-7,8,11,12-tetrahydroheptahelicene in 40% ee. Optically pure ( -)-( M)- and optically highly enriched (+)-( P)- heptahelicene were obtained on a milligram scale by resolution of racemate by chiral HPLC on a semipreparative Whelk-O1 column.

引用

页码：1256 / 1264

页数：9

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