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• W1964684784 endingPage "2879" @default.
• W1964684784 startingPage "2867" @default.
• W1964684784 abstract "Abstract A high stereochemical induction has often been observed in the reduction of ketones with stereogenic centres close to the carbonyl function. The level of stereoselectivity is particularly high when “hard” donor groups such as nitrogen or oxygen atoms are present in the molecule. These results have been commonly explained in terms of a chelate‐controlled process. However, this interpretation has recently been challenged, and in many cases an open‐chain mechanism can better account for the observed results. Thus, Lewis‐acid‐mediated chelation and nonchelation control is one of the most fundamental and practical concepts in transferring a nucleophile moiety to carbonyl compounds. In order to clarify the role of a hard Lewis acid in controlling the stereochemical outcome of a given reaction, the Lewis acid mediated reduction of a series of α‐alkyl‐β‐functionalized carbonyl compounds with metallic hydrides in various solvents was recently investigated. In particular, the results derived from the reductions in the presence of dry CeCl 3 were compared to those obtained under the same experimental conditions but in the presence of TiCl 4 , whose ability to form chelation complexes is well established. These investigations show a stereochemical outcome that is fully consistent with a chelation‐controlled pathway in the case of titanium, and an open‐chain‐controlled pathway in the case of CeCl 3 . The strongly chelating TiCl 4 led to the syn isomer in high diastereomeric excess in noncoordinating solvents at –78 °C with borane–Lewis base complex reducing agents, while nonchelating CeCl 3 produced a high excess of the anti isomer in coordinating solvents at the same temperature with metal borohydrides as reducing agent. Therefore, our method based on the choice of CeCl 3 or TiCl 4 as a Lewis acid under the reported conditions represents a significant contribution to the development of new stereoselective reductions of α‐alkyl‐β‐functionalized ketones. These procedures are one of the best known ways to obtain an alcoholic moiety. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)" @default.
• W1964684784 created "2016-06-24" @default.
• W1964684784 creator A5033648977 @default.
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• W1964684784 creator A5077379747 @default.
• W1964684784 creator A5083398018 @default.
• W1964684784 date "2005-07-01" @default.
• W1964684784 modified "2023-10-03" @default.
• W1964684784 title "Diastereoselective Lewis Acid Mediated Reductions of α‐Alkyl‐β‐Functionalized Carbonyl Compounds" @default.
• W1964684784 cites W112454059 @default.
• W1964684784 cites W120376017 @default.
• W1964684784 cites W1508571065 @default.
• W1964684784 cites W1566080486 @default.
• W1964684784 cites W1574766204 @default.
• W1964684784 cites W1596226296 @default.
• W1964684784 cites W1966258995 @default.
• W1964684784 cites W1971784625 @default.
• W1964684784 cites W1976655311 @default.
• W1964684784 cites W1977534424 @default.
• W1964684784 cites W1977875137 @default.
• W1964684784 cites W1979559201 @default.
• W1964684784 cites W1980348750 @default.
• W1964684784 cites W1980777437 @default.
• W1964684784 cites W1984498166 @default.
• W1964684784 cites W1987026350 @default.
• W1964684784 cites W1993800646 @default.
• W1964684784 cites W1995642476 @default.
• W1964684784 cites W1995821827 @default.
• W1964684784 cites W1996113185 @default.
• W1964684784 cites W1998995909 @default.
• W1964684784 cites W1999135616 @default.
• W1964684784 cites W1999597015 @default.
• W1964684784 cites W2003088088 @default.
• W1964684784 cites W2003862801 @default.
• W1964684784 cites W2013273844 @default.
• W1964684784 cites W2016109081 @default.
• W1964684784 cites W2020844860 @default.
• W1964684784 cites W2022009422 @default.
• W1964684784 cites W2025490101 @default.
• W1964684784 cites W2027173246 @default.
• W1964684784 cites W2031348074 @default.
• W1964684784 cites W2031418081 @default.
• W1964684784 cites W2031845588 @default.
• W1964684784 cites W2038147624 @default.
• W1964684784 cites W2042690824 @default.
• W1964684784 cites W2043397495 @default.
• W1964684784 cites W2044399364 @default.
• W1964684784 cites W2044568919 @default.
• W1964684784 cites W2044623944 @default.
• W1964684784 cites W2045738449 @default.
• W1964684784 cites W2046427107 @default.
• W1964684784 cites W2047388089 @default.
• W1964684784 cites W2052077294 @default.
• W1964684784 cites W2053854247 @default.
• W1964684784 cites W2056340277 @default.
• W1964684784 cites W2058603204 @default.
• W1964684784 cites W2059411924 @default.
• W1964684784 cites W2060390716 @default.
• W1964684784 cites W2061075882 @default.
• W1964684784 cites W2064074436 @default.
• W1964684784 cites W2068107240 @default.
• W1964684784 cites W2075037101 @default.
• W1964684784 cites W2078884047 @default.
• W1964684784 cites W2080811328 @default.
• W1964684784 cites W2081214633 @default.
• W1964684784 cites W2082731919 @default.
• W1964684784 cites W2082998932 @default.
• W1964684784 cites W2086120597 @default.
• W1964684784 cites W2086404667 @default.
• W1964684784 cites W2086817741 @default.
• W1964684784 cites W2087438617 @default.
• W1964684784 cites W2087697002 @default.
• W1964684784 cites W2093728286 @default.
• W1964684784 cites W2093821850 @default.
• W1964684784 cites W2109898499 @default.
• W1964684784 cites W2111660884 @default.
• W1964684784 cites W2113232707 @default.
• W1964684784 cites W2114152356 @default.
• W1964684784 cites W2115676169 @default.
• W1964684784 cites W2120771616 @default.
• W1964684784 cites W2131909314 @default.
• W1964684784 cites W2141447305 @default.
• W1964684784 cites W2141964245 @default.
• W1964684784 cites W2142140776 @default.
• W1964684784 cites W2145644459 @default.
• W1964684784 cites W2148648077 @default.
• W1964684784 cites W2157987891 @default.
• W1964684784 cites W2158483195 @default.
• W1964684784 cites W2168138303 @default.
• W1964684784 cites W2171635127 @default.
• W1964684784 cites W2313235670 @default.
• W1964684784 cites W2476522264 @default.
• W1964684784 cites W2949120183 @default.
• W1964684784 cites W2949125867 @default.
• W1964684784 cites W2949398698 @default.
• W1964684784 cites W2949554610 @default.
• W1964684784 cites W2949755083 @default.

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