Enantioselective Michael Addition of 4‐Hydroxycoumarins to β,γ‐Unsaturated α‐Oxophosphonates Catalysed by a Bifunctional Squaramide Bearing a Structurally Rigid 9,10‐Ethylene‐9,10‐dihydroanthracene Skeleton | Zendy

Chang Xufang | Zendy; Wang Qiaohui | Zendy; Wang Youming | Zendy; Song Haibin | Zendy; Zhou Zhenghong | Zendy; Tang Chuchi | Zendy

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Enantioselective Michael Addition of 4‐Hydroxycoumarins to β,γ‐Unsaturated α‐Oxophosphonates Catalysed by a Bifunctional Squaramide Bearing a Structurally Rigid 9,10‐Ethylene‐9,10‐dihydroanthracene Skeleton

Author(s) -

Chang Xufang,

Wang Qiaohui,

Wang Youming,

Song Haibin,

Zhou Zhenghong,

Tang Chuchi

Publication year - 2013

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201201573

Subject(s) - squaramide , bifunctional , chemistry , enantioselective synthesis , michael reaction , nucleophile , amine gas treating , organocatalysis , quenching (fluorescence) , organic chemistry , medicinal chemistry , catalysis , physics , quantum mechanics , fluorescence

A bifunctional squaramide based on ( R , R )‐11,12‐diamino‐9,10‐ethylene‐9,10‐dihydroanthracene has been developed, and it has demonstrated great advantages over previously reported organocatalysts in the asymmetric Michael addition of 4‐hydroxycoumarins to β,γ‐unsaturated α‐oxophosphonates. Upon quenching the generated β‐4‐hydroxy‐2‐oxo‐2 H ‐chromen‐3‐yl‐substituted acylphosphonate intermediates with DBU and an alcohol or amine as a second nucleophile, the corresponding β‐substituted carboxylates or amides were obtained in acceptable to excellent yields and with high levels of enantioselectivity (80–97 % ee ) in a one‐pot fashion.

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