Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 8, Pages 2474-2478Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201812266
Keywords
asymmetric synthesis; conjugate addition; ligand design; rhodium; spirocycles
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Funding
- National Natural Science Foundation of China [21602253]
- Natural Science Foundation of Jiangsu Province [BK20160749]
- Double First-Class University project [CPU2018GY35, CPU2018GF02]
- Ministry of Education (MOE) of Singapore [MOE2017-T2-1-064]
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The enantioselective synthesis of a series of C-2-symmetric 3,3 '-diarylated 1,1 '-spirobiindane-7,7 '-diols (3,3 '-diaryl-SPINOLs) was developed by sequential Rh-catalyzed twofold asymmetric conjugate arylation/BF3-promoted diastereoselective spirocyclization (>20:1 d.r. and >99 % ee for all examples). Some phosphoramidite ligands were prepared from the 3,3 '-Ph-SPINOL and applied to several catalytic asymmetric reactions, and the 3,3 '-diarylated ligands showed higher enantioselectivities than the privileged nonsubstituted ligands.
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