Aryloxymethyltrifluoroborates for Rhodium-Catalyzed Asymmetric Conjugate Arylation. o-Methoxyarylation through 1,4-Rhodium Shift.

Author(s) Ming, J.; Hayashi, T.
Journal Org Lett
Date Published 2016 Dec 16

Reaction of potassium aryloxymethyltrifluoroborates 1 with α,β-unsaturated carbonyl compounds 2 in the presence of a chiral diene-rhodium catalyst in H2O at 100 °C introduced 2-methoxyaryl groups at the β-position of 2 with high enantioselectivity in high yields. The reaction is assumed to proceed through 1,4-Rh shift from aryloxymethyl-Rh intermediate to 2-methoxyaryl-Rh. The high availability of phenol derivatives makes this asymmetric conjugate arylation synthetically useful.

DOI 10.1021/acs.orglett.6b03347
ISSN 1523-7052
Citation Org Lett. 2016;18(24):64526455.

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