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- W1987702285 endingPage "17088" @default.
- W1987702285 startingPage "17077" @default.
- W1987702285 abstract "Abstract The effect of silyl substituents in diphenylprolinol silyl ether catalysts was investigated. Mechanistically, reactions catalyzed by diphenylprolinol silyl ether can be categorized into three types: two that involve an iminium ion intermediate, such as for the Michael‐type reaction (type A) and the cycloaddition reaction (type B), and one that proceeds via an enamine intermediate (type C). In the Michael‐type reaction via iminium ions (type A), excellent enantioselectivity is realized when the catalyst with a bulky silyl moiety is employed, in which efficient shielding of a diastereotopic face of the iminium ion is directed by the bulky silyl moiety. In the cycloaddition reaction of iminium ions (type B) and reactions via enamines (type C), excellent enantioselectivity is obtained even when the silyl group is less bulky and, in this case, too much bulk reduces the reaction rate. In other cases, the yield increases when diphenylprolinol silyl ethers with bulky substituents are employed, presumably by suppressing side reactions between the nucleophilic catalyst and the reagent. The conformational behaviors of the iminium and enamine species have been determined by theoretical calculations. These data explain the effect of the bulkiness of the silyl substituent on the enantioselectivity and reactivity of the catalysts." @default.
- W1987702285 created "2016-06-24" @default.
- W1987702285 creator A5035476970 @default.
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- W1987702285 creator A5085481187 @default.
- W1987702285 creator A5022462717 @default.
- W1987702285 date "2014-10-27" @default.
- W1987702285 modified "2023-10-18" @default.
- W1987702285 title "A Theoretical and Experimental Study of the Effects of Silyl Substituents in Enantioselective Reactions Catalyzed by Diphenylprolinol Silyl Ether" @default.
- W1987702285 cites W1516205559 @default.
- W1987702285 cites W1587648185 @default.
- W1987702285 cites W1966498599 @default.
- W1987702285 cites W1969746639 @default.
- W1987702285 cites W1969921245 @default.
- W1987702285 cites W1974879112 @default.
- W1987702285 cites W1975410532 @default.
- W1987702285 cites W1980521165 @default.
- W1987702285 cites W1980883950 @default.
- W1987702285 cites W1982356449 @default.
- W1987702285 cites W1990971813 @default.
- W1987702285 cites W2008754069 @default.
- W1987702285 cites W2013821889 @default.
- W1987702285 cites W2016571924 @default.
- W1987702285 cites W2018758670 @default.
- W1987702285 cites W2019276736 @default.
- W1987702285 cites W2023271753 @default.
- W1987702285 cites W2030219315 @default.
- W1987702285 cites W2031588396 @default.
- W1987702285 cites W2040384768 @default.
- W1987702285 cites W2044948223 @default.
- W1987702285 cites W2046615311 @default.
- W1987702285 cites W2050346320 @default.
- W1987702285 cites W2055334921 @default.
- W1987702285 cites W2057491831 @default.
- W1987702285 cites W2059073029 @default.
- W1987702285 cites W2070365089 @default.
- W1987702285 cites W2071579644 @default.
- W1987702285 cites W2074417368 @default.
- W1987702285 cites W2074484156 @default.
- W1987702285 cites W2074510303 @default.
- W1987702285 cites W2080303261 @default.
- W1987702285 cites W2082972031 @default.
- W1987702285 cites W2086202444 @default.
- W1987702285 cites W2086574960 @default.
- W1987702285 cites W2086957099 @default.
- W1987702285 cites W2087710238 @default.
- W1987702285 cites W2089775150 @default.
- W1987702285 cites W2090850464 @default.
- W1987702285 cites W2095405339 @default.
- W1987702285 cites W2101288392 @default.
- W1987702285 cites W2103118742 @default.
- W1987702285 cites W2109441504 @default.
- W1987702285 cites W2111280484 @default.
- W1987702285 cites W2112827424 @default.
- W1987702285 cites W2113764675 @default.
- W1987702285 cites W2115155358 @default.
- W1987702285 cites W2119406720 @default.
- W1987702285 cites W2122213248 @default.
- W1987702285 cites W2126169089 @default.
- W1987702285 cites W2127520966 @default.
- W1987702285 cites W2127636836 @default.
- W1987702285 cites W2129579634 @default.
- W1987702285 cites W2135428667 @default.
- W1987702285 cites W2143981217 @default.
- W1987702285 cites W2144007525 @default.
- W1987702285 cites W2145448376 @default.
- W1987702285 cites W2147329892 @default.
- W1987702285 cites W2150697053 @default.
- W1987702285 cites W2151365162 @default.
- W1987702285 cites W2155203592 @default.
- W1987702285 cites W2155972237 @default.
- W1987702285 cites W2156974079 @default.
- W1987702285 cites W2158454017 @default.
- W1987702285 cites W2166149654 @default.
- W1987702285 cites W2166399067 @default.
- W1987702285 cites W2321908925 @default.
- W1987702285 cites W2323080246 @default.
- W1987702285 cites W2324033421 @default.
- W1987702285 cites W2329449159 @default.
- W1987702285 cites W2330355294 @default.
- W1987702285 cites W2335344650 @default.
- W1987702285 cites W2428894216 @default.
- W1987702285 cites W4211250191 @default.
- W1987702285 cites W4230596967 @default.
- W1987702285 cites W4234412669 @default.
- W1987702285 cites W4235344967 @default.
- W1987702285 cites W4235846569 @default.
- W1987702285 cites W4238774485 @default.
- W1987702285 cites W4240766220 @default.
- W1987702285 cites W4240964525 @default.
- W1987702285 cites W4243284524 @default.
- W1987702285 cites W4243321906 @default.
- W1987702285 cites W4246757389 @default.
- W1987702285 cites W4254090296 @default.