Monoselective o‑C–H Functionalizations of Mandelic Acid and α‑Phenylglycine

Pd-catalyzed C–H functionalization of mandelic acid and α-phenylglycine is reported. We have developed different protocols for the arylation, iodination, acetoxylation, and olefination of these substrates based on two different (Pd­(II)/Pd­(IV) and Pd­(II)/Pd(0)) catalytic cycles. Four crucial featu...

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Veröffentlicht in:Journal of the American Chemical Society 2015-08, Vol.137 (31), p.9877-9884
Hauptverfasser: Dastbaravardeh, Navid, Toba, Tetsuya, Farmer, Marcus E, Yu, Jin-Quan
Format: Artikel
Sprache:eng
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Zusammenfassung:Pd-catalyzed C–H functionalization of mandelic acid and α-phenylglycine is reported. We have developed different protocols for the arylation, iodination, acetoxylation, and olefination of these substrates based on two different (Pd­(II)/Pd­(IV) and Pd­(II)/Pd(0)) catalytic cycles. Four crucial features of these protocols are advantageous for practical applications. First, the α-hydroxyl and amino groups are protected with simple protecting groups such as acetates (Ac, Piv) and carbamates (Boc, Fmoc), respectively. Second, these protocols do not involve installation and removal of a directing group. Third, monoselectivity is accomplished. Fourth, no epimerization occurs at the vulnerable α-chiral centers.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.5b04324