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Enantioselective Synthesis of 4-Methyl-3,4-dihydroisocoumarin via Asymmetric Hydroformylation of Styrene Derivatives

Author:
Qu, Bo, Tan, Renchang, Herling, Madison R., Haddad, Nizar, Grinberg, Nelu, Kozlowski, Marisa C., Zhang, Xumu, Senanayake, Chris H.
Source:
Journal of organic chemistry 2019 v.84 no.8 pp. 4915-4920
ISSN:
1520-6904
Subject:
aldehydes, chemical reactions, chemical structure, enantioselective synthesis, ligands, organic chemistry, styrene
Abstract:
Enantioenriched aldehydes are produced through asymmetric hydroformylation of styrene derivatives using BIBOP-type ligands. The featured example is enantioselective synthesis of 4-methyl-3,4-dihydroisocoumarin, which was prepared in a 95.1:4.9 enantiomeric ratio from asymmetric hydroformylation of ethyl 2-vinylbenzoate followed by in situ lactonization during the reduction process. The conditions are compatible with both electron-rich and electron-poor substituents.
Agid:
6375887