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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.