65948-15-4Relevant academic research and scientific papers
Identification of an Esterase Isolated Using Metagenomic Technology which Displays an Unusual Substrate Scope and its Characterisation as an Enantioselective Biocatalyst
Gavin, Declan P.,Murphy, Edel J.,Foley, Aoife M.,Castilla, Ignacio Abreu,Reen, F. Jerry,Woods, David F.,Collins, Stuart G.,O'Gara, Fergal,Maguire, Anita R.
supporting information, p. 2466 - 2474 (2019/03/11)
Evaluation of an esterase annotated as 26D isolated from a marine metagenomic library is described. Esterase 26D was found to have a unique substrate scope, including synthetic transformations which could not be readily effected in a synthetically useful manner using commercially available enzymes. Esterase 26D was more selective towards substrates which had larger, more sterically demanding substituents (i. e. iso-propyl or tert-butyl groups) on the β-carbon, which is in contrast to previously tested commercially available enzymes which displayed a preference for substrates with sterically less demanding substituents (e.g. methyl group) at the β-carbon. (Figure presented.).
Rhodium-Catalyzed Enantioselective Defluorinative α-Arylation of Secondary Amides
Jang, Young Jin,Rose, Daniel,Mirabi, Bijan,Lautens, Mark
supporting information, p. 16147 - 16151 (2018/11/23)
We exploited the reactivity of an electronically biased Michael acceptor to perform a defluorinative α-arylation reaction using a chiral diene(L*)-rhodium catalyst. Through this methodology, we are able to obtain various secondary amides, containing a tertiary α-stereocenter and a β,γ-unsaturated gem-difluoro olefin, with excellent enantioselectivities. This methodology addresses the limitations of the previously described α-arylation methods to construct stereo-labile tertiary α-stereocenters. Further investigation of the reaction via in situ 19F NMR monitoring suggests that the formation of the product leads to the inhibition of the active rhodium catalyst.
Rhodium(i)-catalyzed 1,4-conjugate arylation toward β-fluoroalkylated electron-deficient alkenes: A new entry to a construction of a tertiary carbon center possessing a fluoroalkyl group
Morigaki, Atsunori,Tanaka, Tomoo,Miyabe, Tomotsugu,Ishihara, Takashi,Konno, Tsutomu
, p. 586 - 595 (2013/03/14)
Treatment of β-fluoroalkylated-α,β-unsaturated ketones with 1.2 equiv. of various arylboronic acids in the presence of 5 mol% of [Rh(COD)2]BF4 and 6 mol% of (S)-BINAP in toluene/H 2O (v/v = 4/1) at the reflux temperature for 3 h gave the corresponding Michael adducts in high yields with over 90% enantioselectivity. Though other electron-deficient alkenes, such as vinylsulfone and vinylphosphonate, were found to be much less reactive in the rhodium-catalyzed conjugate addition with arylboronic acids, the reaction of various arylstannanes toward such electron-deficient alkenes took place very smoothly to afford the corresponding adducts in high yields.
Unexpected high regiocontrol in Heck reaction of fluorine-containing electron-deficient olefins-Highly regio- and stereoselective synthesis of β-fluoroalkyl-α-aryl-α,β-unsaturated ketones
Konno, Tsutomu,Yamada, Shigeyuki,Tani, Akinori,Nishida, Masataka,Miyabe, Tomotsugu,Ishihara, Takashi
experimental part, p. 913 - 921 (2010/01/15)
Treatment of (E)-4,4,4-trifluoro-1-aryl-2-buten-1-one with various aryldiazonium salts in the presence of palladium catalyst gave the corresponding α-arylated Heck adducts with high regio- and stereoselectivity in good to high yields.
A first high enantiocontrol of an asymmetric tertiary carbon center attached with a fluoroalkyl group via Rh(I)-catalyzed conjugate addition reaction
Konno, Tsutomu,Tanaka, Tomoo,Miyabe, Tomotsugu,Morigaki, Atsunori,Ishihara, Takashi
, p. 2106 - 2110 (2008/09/18)
Treatment of fluoroalkylated electron-deficient olefins with various boronic acids in the presence of a catalytic amount of Rh(I) coordinated with (S)-BINAP in toluene/H2O at the reflux temperature for 3 h gave the corresponding conjugate addit
