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 |
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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. |
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ISSN: | 0002-7863 1520-5126 1520-5126 |
DOI: | 10.1021/jacs.5b04324 |