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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) 2 NEt in THF at 60 8C 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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Author

Wei-Min Dai; Kelly Ka Yim Yeung; Yongqiang Wang

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

2004

Language

EN

Field

Chemistry (Physical Sciences)