Selectivity Manipulation of Bicyclization Reactions of 1,5‐Bis(1,2‐allenylketone)s: Pd versus Rh and Electronic Effect | Zendy

Deng Youqian | Zendy; Fu Chunling | Zendy; Ma Shengming | Zendy

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Selectivity Manipulation of Bicyclization Reactions of 1,5‐Bis(1,2‐allenylketone)s: Pd versus Rh and Electronic Effect

Author(s) -

Deng Youqian,

Fu Chunling,

Ma Shengming

Publication year - 2011

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201003546

Subject(s) - selectivity , rhodium , acetone , chemistry , medicinal chemistry , combinatorial chemistry , computer science , stereochemistry , catalysis , organic chemistry

Select Rh! The rhodium(I)‐catalyzed double cyclization of 1,5‐bis(1,2‐allenylketone)s gives TNF‐α inhibitor (A)‐type skeletons at room temperature in acetone or 1,2‐dichloroethane (DCE, see scheme; Ts=Tosyl). Compared with [PdCl 2 (MeCN) 2 ], [RhCl(CO) 2 ] 2 shows excellent selectivity towards the nonaromatic CC bond. The selectivity of unsymmetrical substrates can be controlled by the electronic effect.

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