Synthesis of New Phosphahelicene Scaffolds and Development of Gold(I)-Catalyzed Enantioselective Allenene Cyclizations

被引:46
作者
Aillard, Paul [1 ]
Retailleau, Pascal [1 ]
Voituriez, Arnaud [1 ]
Marinetti, Angela [1 ]
机构
[1] Univ Paris 11, Inst Chim Subst Nat, ICSN CNRS UPR 2301, F-91198 Gif Sur Yvette, France
关键词
cyclotrimerization; allenenes; enantioselectivity; gold catalysis; phosphahelicenes; GOLD CATALYSIS; 2+2+2 CYCLOISOMERIZATION; ASYMMETRIC CATALYSIS; MOLECULES; CYCLOADDITIONS; HELICENES; LIGANDS; UNITS; DERIVATIVES; CHIRALITY;
D O I
10.1002/chem.201501697
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This paper reports on the development of an efficient synthesis of enantiopure phospha[6]helicenes through a [2+2+2] alkyne cyclotrimerization reaction. The corresponding gold complexes proved to be highly efficient both in terms of catalytic activity and enantioselectivity in [2+2] and [4+2] cycloaddition reactions. Furthermore, in the presence of an external nucleophile, such as water or alcohols, the tandem cyclization/addition reactions take place in high yields and excellent diastereo- and enantioselectivities.
引用
收藏
页码:11989 / 11993
页数:5
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