170700-71-7Relevant academic research and scientific papers
Ir(I)-catalyzed enantioselective decarboxylative allylic etherification: A general method for the asymmetric synthesis of aryl allyl ethers
Kim, Dongeun,Reddy, Srinivasa,Singh, Om V.,Lee, Jae Seung,Kong, Suk Bin,Han, Hyunsoo
, p. 512 - 515 (2013/04/10)
Ir(I)-catalyzed enantioselective decarboxylative allylic etherification of aryl allyl carbonates provides aryl allyl ethers. Key to the generality and high stereoselection of the reaction is the use of the intramolecular decarboxylative allylation process
Stereoconvergent synthesis of chiral allylboronates from an E/Z mixture of allylic aryl ethers using a 6-NHC-Cu(I) catalyst
Park, Jin Kyoon,Lackey, Hershel H.,Ondrusek, Brian A.,McQuade, D. Tyler
supporting information; experimental part, p. 2410 - 2413 (2011/04/25)
We present a 6-NHC-Cu(I) complex that provides α-substituted allylboronates using allylic aryl ether substrates. The method was discovered by comparison of the chemoselectivities exhibited by complexes 1a, 1b, 2, and 3. We observed that 1a preferentially reacts with electron-rich alkenes over electron-deficient alkenes. Development of an asymmetric method revealed that 1b reacts with both the E and Z isomers to provide the same absolute configuration without showing E-Z isomerization. This stereoconvergent reaction occurs with high yields (av 86%), high SN2′ selectivity (>99:1), and high ee (av 94%) and exhibits wide functional-group tolerance using pure E or Z isomer or E/Z alkene mixtures. The stereoconvergent feature enables the use of many different olefination strategies for substrate production, including cross-metathesis. Chiral allylboronates could be purified by silica gel chromatography and stored in the freezer without decomposition.
Synthesis and reactivity of complexes 2a-c, their involvement as catalyst precursors for regioselective allylic substitution reactions and related [Ru(Cp*)Cl(Ph2POMe)(RCHCHCH2)] [PF6] η3-allyl ruthenium(IV)inter
Demerseman, Bernard,Renaud, Jean-Luc,Toupet, Loic,Hubert, Claudie,Bruneau, Christian
, p. 1371 - 1380 (2007/10/03)
The synthesis of the new complexes [Ru(Cp*)(L)(MeCN) 2]-[PF6] (L = Ph2POMe or Ph2P-o- tolyl) and {Ru(Cp*)-[Ph2PCH2C(tBu)=O](MeCN)}[PF 6] (2a-c) is achieved starting from [Ru(Cp*)
Effects of catalyst activation and ligand steric properties on the enantioselective allylation of amines and phenoxides
Leitner, Andreas,Shu, Chutian,Hartwig, John F.
, p. 1093 - 1096 (2007/10/03)
(Chemical Equation Presented) The yields, enantioselectivities, and regioselectivities of the reactions of amines and phenoxides with allylic carbonates in the presence of a metallacyclic iridium catalyst were compared. These data show that both preactiva
Regio- and enantioselective iridium-catalyzed intermolecular allylic etherification of achiral allylic carbonates with phenoxides
Lopez, Fernando,Ohmura, Toshimichi,Hartwig, John F.
, p. 3426 - 3427 (2007/10/03)
An enantioselective and regioselective iridium-catalyzed allylic etherification is described. The reaction of sodium and lithium aryloxides with achiral (E)-cinnamyl and terminal aliphatic allylic electrophiles in the presence of 2 mol % of an iridium-phosphoramidite complex provides chiral allylic aryl ethers in high yields and excellent levels of regio- and enantioselectivity. Lithium aryloxides containing a single substituent at an ortho, meta, or para position as well as sterically hindered phenoxides were tolerated. Reactions in THF displayed the most suitable balance of rate, regio-, and enantioselectivity. High ee's were also observed for the products from the reaction of alkyl (E)-allylic carbonates. Copyright
