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- W2969551427 endingPage "6605" @default.
- W2969551427 startingPage "6597" @default.
- W2969551427 abstract "A general and efficient synthesis of α‐haloglycine esters from commercially available feedstock chemicals, in a single step, is reported. The reactivity of these α‐haloglycine esters with various nucleophiles was studied as surrogates of α‐iminoesters upon activation with hydrogen‐bond donor catalysts. DFT calculations on the α‐haloglycine structures (X = F, Cl, Br) accompanied by an X‐ray characterization of the α‐bromoglycine ester support the existence of a “generalized” anomeric effect created by hyperconjugation. This peculiar hyperconjugative effect is proposed to be responsible for the enhanced halogen nucleofugality leading to a facile halogen abstraction by hydrogen‐bond donor catalysts. This reactivity was exploited with thiourea catalysts on several catalytic transformations (aza‐Friedel–Crafts and Mannich reactions) for the synthesis of several types of non‐proteinogenic α‐amino esters." @default.
- W2969551427 created "2019-08-29" @default.
- W2969551427 creator A5076307675 @default.
- W2969551427 creator A5088229078 @default.
- W2969551427 date "2019-09-17" @default.
- W2969551427 modified "2023-10-14" @default.
- W2969551427 title "Synthesis and Reactivity of α-Haloglycine Esters: Hyperconjugation in Action" @default.
- W2969551427 cites W1963951918 @default.
- W2969551427 cites W1965704764 @default.
- W2969551427 cites W1970065130 @default.
- W2969551427 cites W1978577690 @default.
- W2969551427 cites W1979813209 @default.
- W2969551427 cites W1980855716 @default.
- W2969551427 cites W1982009575 @default.
- W2969551427 cites W1982061522 @default.
- W2969551427 cites W1983893318 @default.
- W2969551427 cites W1986533400 @default.
- W2969551427 cites W1990659407 @default.
- W2969551427 cites W1991989818 @default.
- W2969551427 cites W1992590756 @default.
- W2969551427 cites W2003567979 @default.
- W2969551427 cites W2004483101 @default.
- W2969551427 cites W2005540985 @default.
- W2969551427 cites W2007729122 @default.
- W2969551427 cites W2008733674 @default.
- W2969551427 cites W2010120895 @default.
- W2969551427 cites W2013676686 @default.
- W2969551427 cites W2014521318 @default.
- W2969551427 cites W2014555901 @default.
- W2969551427 cites W2022366997 @default.
- W2969551427 cites W2022367554 @default.
- W2969551427 cites W2023040540 @default.
- W2969551427 cites W2023045222 @default.
- W2969551427 cites W2026528307 @default.
- W2969551427 cites W2027589805 @default.
- W2969551427 cites W2033192042 @default.
- W2969551427 cites W2034475135 @default.
- W2969551427 cites W2038602425 @default.
- W2969551427 cites W2040019715 @default.
- W2969551427 cites W2043351993 @default.
- W2969551427 cites W2045973123 @default.
- W2969551427 cites W2046358340 @default.
- W2969551427 cites W2046971493 @default.
- W2969551427 cites W2047129407 @default.
- W2969551427 cites W2047592228 @default.
- W2969551427 cites W2048200123 @default.
- W2969551427 cites W2049655345 @default.
- W2969551427 cites W2049779382 @default.
- W2969551427 cites W2050000500 @default.
- W2969551427 cites W2052671506 @default.
- W2969551427 cites W2053111307 @default.
- W2969551427 cites W2053351141 @default.
- W2969551427 cites W2055455250 @default.
- W2969551427 cites W2056224613 @default.
- W2969551427 cites W2056971171 @default.
- W2969551427 cites W2057482737 @default.
- W2969551427 cites W2057717450 @default.
- W2969551427 cites W2057930453 @default.
- W2969551427 cites W2058028743 @default.
- W2969551427 cites W2064967571 @default.
- W2969551427 cites W2066103357 @default.
- W2969551427 cites W2066284211 @default.
- W2969551427 cites W2066678751 @default.
- W2969551427 cites W2067369495 @default.
- W2969551427 cites W2068802714 @default.
- W2969551427 cites W2069913189 @default.
- W2969551427 cites W2070481836 @default.
- W2969551427 cites W2070819492 @default.
- W2969551427 cites W2073651308 @default.
- W2969551427 cites W2074811818 @default.
- W2969551427 cites W2075503855 @default.
- W2969551427 cites W2075812374 @default.
- W2969551427 cites W2076749281 @default.
- W2969551427 cites W2078033380 @default.
- W2969551427 cites W2081021457 @default.
- W2969551427 cites W2081088414 @default.
- W2969551427 cites W2081747899 @default.
- W2969551427 cites W2082225930 @default.
- W2969551427 cites W2083467029 @default.
- W2969551427 cites W2083811591 @default.
- W2969551427 cites W2084584863 @default.
- W2969551427 cites W2088767741 @default.
- W2969551427 cites W2089387775 @default.
- W2969551427 cites W2092745111 @default.
- W2969551427 cites W2095204901 @default.
- W2969551427 cites W2100328667 @default.
- W2969551427 cites W2106064727 @default.
- W2969551427 cites W2107780973 @default.
- W2969551427 cites W2114303865 @default.
- W2969551427 cites W2118519947 @default.
- W2969551427 cites W2119670735 @default.
- W2969551427 cites W2122903273 @default.
- W2969551427 cites W2123557766 @default.
- W2969551427 cites W2123659522 @default.
- W2969551427 cites W2134220661 @default.
- W2969551427 cites W2138521445 @default.
- W2969551427 cites W2139907799 @default.
- W2969551427 cites W2143660327 @default.