Heterocyclic Spiranes and Dispiranes via Enantioselective Phosphine-Catalyzed [3+2]?Annulations

被引：42
|
作者：
Duvvuru, Deepti [1 ]
Pinto, Nathalie [1 ]
Gomez, Catherine [1 ]
Betzer, Jean-Francois [1 ]
Retailleau, Pascal [1 ]
Voituriez, Arnaud [1 ]
Marinetti, Angela [1 ]
机构：
[1] Ctr Rech Gif, CNRS, UPR 2301, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 2-3期
关键词：
3+2]?cyclization; enantioselective organocatalysis; phosphines; spiro compounds; sulfoxides; ASYMMETRIC 3+2 CYCLOADDITION; ELECTRON-DEFICIENT OLEFINS; FUNCTIONALIZED CYCLOPENTENES; ANTIMYCOBACTERIAL EVALUATION; 1,3-DIPOLAR CYCLOADDITION; CONTAINING LIGANDS; GLUTAMATE ANALOGS; CYCLIZATIONS; SULFOXIDES; EFFICIENT;
D O I：
10.1002/adsc.201100748
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The synthesis of highly functionalized heterocyclic spiranes has been carried out by [3+2] cyclizations between allenoates and enones, under phosphine catalysis. Excellent enantioselectivity levels (ees up to 99%) have been attained in FerroPHANE-promoted cyclizations of this class, leading to chiral sulfides with unprecedented spiranic structures. The corresponding sulfoxides have been obtained then via a subsequent, highly diastereoselective oxidation of the prostereogenic sulfur centre.
引用
收藏
页码：408 / 414
页数：7
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