Synthesis of 3-Hydroxymethyl Isoindolinones via Cobalt-Catalyzed C(sp(2))-H Carbonylation of Phenylglycinol Derivatives

Organic Letters 2020
Lūkass Tomass Lukašēvics, Aleksandrs Cizikovs, Liene Grigorjeva

An efficient method for the synthesis of 3-hydroxymethyl isoindolinones via cobalt-catalyzed C(sp2)-H carbonylation of phenylglycinol derivatives using picolinamide as a traceless directing group is demonstrated. The reaction proceeds in the presence of a commercially available cobalt(II) tetramethylheptanedionate catalyst and employs DIAD as a "CO" surrogate. This synthetic route offers a broad substrate scope, excellent regioselectivity, and full preservation of the original stereochemistry. Besides, the developed method provides a pathway for accessing valuable enantiopure 3-substituted isoindolinone derivatives.

DOI
10.1021/acs.orglett.0c00672
Hyperlink
https://pubs.acs.org/doi/10.1021/acs.orglett.0c00672

Lukašēvics, L., Cizikovs, A., Grigorjeva, L. Synthesis of 3-Hydroxymethyl Isoindolinones via Cobalt-Catalyzed C(sp(2))-H Carbonylation of Phenylglycinol Derivatives. Organic Letters, 2020, Vol. 22, No. 7, pp.2720-2723. ISSN 1523-7060. e-ISSN 1523-7052. Available from: doi:10.1021/acs.orglett.0c00672

Publication language
English (en)