The first example of atropisomeric amide-derived P,O-ligands used for an asymmetric Heck reaction |
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| Authors: | Wei-Min Dai Kelly Ka Yim Yeung Yongqiang Wang |
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| Institution: | Department of Chemistry and Open Laboratory of Chirotechnology of The Institute of Molecular Technology for Drug Discovery and Synthesis, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China |
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| Abstract: | Atropisomeric N,N-diisopropyl 2-diphenylphosphino- and 2-di(tert-butyl)phosphino-1-naphthamides were used, for the first time, as bidentate P,O-ligands for intermolecular asymmetric Heck reactions of 2,3-dihydrofuran with aryl triflates. The reactions were carried out in the presence of 4 mol% Pd(OAc)2, 8 mol% of the axially chiral ligand, and 3 equiv. of (i-Pr)2NEt in THF at 60 °C for 3 days. Optically active 2-aryl-2,5-dihydrofurans were obtained as the major products along with the rearranged 2-aryl-2,3-dihydrofurans. Enantioselectivity up to 55.2% ee was obtained for the major product. |
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| Keywords: | Atropisomerism P O-ligand Asymmetric Heck reaction Dihydrofuran Palladium |
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