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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| container_issue | 31 |
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| container_title | Journal of the American Chemical Society |
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| creator | Dastbaravardeh, Navid Toba, Tetsuya Farmer, Marcus E Yu, Jin-Quan |
| description | 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. |
| doi_str_mv | 10.1021/jacs.5b04324 |
| format | Article |
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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. 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Am. Chem. Soc</addtitle><date>2015-08-12</date><risdate>2015</risdate><volume>137</volume><issue>31</issue><spage>9877</spage><epage>9884</epage><pages>9877-9884</pages><issn>0002-7863</issn><issn>1520-5126</issn><eissn>1520-5126</eissn><abstract>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.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26162456</pmid><doi>10.1021/jacs.5b04324</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of the American Chemical Society, 2015-08, Vol.137 (31), p.9877-9884 |
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| source | MEDLINE; ACS Publications |
| subjects | acetates Alkenes - chemistry carbamates Carbon - chemistry Catalysis Glycine - analogs & derivatives Glycine - chemistry Halogenation Hydrogen - chemistry iodination mandelic acid Mandelic Acids - chemistry Palladium - chemistry standard operating procedures Substrate Specificity |
| title | Monoselective o‑C–H Functionalizations of Mandelic Acid and α‑Phenylglycine |
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