Journal
TETRAHEDRON
Volume 75, Issue 2, Pages 269-277Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.11.057
Keywords
Asymmetric catalysis; Intramolecular hydroacylation; Rhodium; Alkenes; Indanones
Categories
Funding
- National Natural Science Foundation of China [21572131, 21620102003]
- Shanghai Municipal Education Commission [201701070002E00030]
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The intramolecular hydroacylation of 1,2-disubstituted alkenes was considered to be a challenging task due to the side reactions resulted from the lack of additional substituent at 1-position and the low activity caused by the steric hindrance of substituent at 2-position, and an asymmetric version has not been considered possible due to problems associated with the racemization of the products. We have partially solved these problems. Catalyzed by an activated diphosphine-Rh complex and reacted in a selected dihalogenated solvent, the intramolecular hydroacylation of o-(2-arylvinyl)benzaldehydes provided the corresponding 2-aryl-1-indanones in high yields, and its asymmetric variant using o-(2-alkylvinyl) benzaldehydes afforded chiral 2-alkyl-1-indanones in high yields and with moderate enantioselectivities. (C) 2018 Elsevier Ltd. All rights reserved.
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