Enantioselective [3 + 2] Cycloaddition of Allenes to Acrylates Catalyzed by Dipeptide-Derived Phosphines: Facile Creation of Functionalized Cyclopentenes Containing Quaternary Stereogenic Centers

Enantioselective [3 + 2] Cycloaddition of Allenes to Acrylates Catalyzed by Dipeptide-Derived Phosphines: Facile Creation of Functionalized Cyclopentenes Containing Quaternary Stereogenic Centers

A new family of dipeptide-based chiral phosphines was designed and prepared. d-Thr-l-tert-Leu-derived catalyst 4c promoted [3 + 2] cycloaddition of allenoates to α-substituted acrylates in a regiospecific and stereoselective manner, furnishing functionalized cyclopentenes with quaternary stereogenic...

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Veröffentlicht in:Journal of the American Chemical Society 2011-02, Vol.133 (6), p.1726-1729
Hauptverfasser: Han, Xiaoyu, Wang, Youqing, Zhong, Fangrui, Lu, Yixin
Format: Artikel
Sprache:eng
Schlagworte:
Acrylates - chemistry
Alkadienes - chemistry
Catalysis
Cyclopentanes - chemistry
Dipeptides - chemistry
Phosphines - chemistry
Stereoisomerism
Substrate Specificity
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Zusammenfassung:A new family of dipeptide-based chiral phosphines was designed and prepared. d-Thr-l-tert-Leu-derived catalyst 4c promoted [3 + 2] cycloaddition of allenoates to α-substituted acrylates in a regiospecific and stereoselective manner, furnishing functionalized cyclopentenes with quaternary stereogenic centers in high yields and with excellent enantioselectivities.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja1106282