Asymmetric Synthesis of cis-4-Aminobenzopyran Derivatives Catalyzed by N,N′-Dioxide-Sc(OTf)3 Complexes

Asymmetric Synthesis of cis-4-Aminobenzopyran Derivatives Catalyzed by N,N′-Dioxide-Sc(OTf)3 Complexes

The reactions of salicylaldimines with electron‐rich alkenes (2,3‐dihydro‐2H‐furan and 3,4‐dihydro‐2H‐pyran) catalyzed by N,N′‐dioxide–Sc(OTf)3 complexes were investigated. The methodology was successfully applied to the asymmetric synthesis of cis‐4‐aminobenzopyran derivatives. Excellent yields, di...

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Veröffentlicht in:Chemistry : a European journal 2011-12, Vol.17 (49), p.13684-13687
Hauptverfasser: Zhang, Yulong, Dong, Shunxi, Liu, Xiaohua, Xie, Mingsheng, Zhu, Yin, Lin, Lili, Feng, Xiaoming
Format: Artikel
Sprache:eng
Schlagworte:
aminobenzopyrans
Benzopyrans - chemical synthesis
Benzopyrans - chemistry
Catalysis
Chemistry
Combinatorial Chemistry Techniques
dioxides
enantioselectivity
Models, Molecular
Molecular Structure
salicylaldimines
scandium
Scandium - chemistry
Stereoisomerism
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Zusammenfassung:The reactions of salicylaldimines with electron‐rich alkenes (2,3‐dihydro‐2H‐furan and 3,4‐dihydro‐2H‐pyran) catalyzed by N,N′‐dioxide–Sc(OTf)3 complexes were investigated. The methodology was successfully applied to the asymmetric synthesis of cis‐4‐aminobenzopyran derivatives. Excellent yields, diastereo‐ and enantioselectivities were observed for a broad range of substrates under mild conditions (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201102058