80352-30-3Relevant academic research and scientific papers
Cobalt-Catalyzed Asymmetric 1,4-Hydroboration of Enones with HBpin
Ren, Xiang,Lu, Zhan
supporting information, p. 8370 - 8374 (2021/11/01)
Herein, a series of new 8-OIQ cobalt complexes were synthesized and used for cobalt-catalyzed chemo- and enantioselective 1,4-hydroboration of enones with HBpin to access chiral β,β-disubstituted ketones with good to excellent chemo- and enantioselectivties. This protocol is operationally simple and shows a broad substrate scope.
Alcohol Dehydrogenases and N-Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β-Disubstituted Allylic Alcohols
González-Granda, Sergio,Lavandera, Iván,Gotor-Fernández, Vicente
supporting information, p. 13945 - 13951 (2021/04/22)
The combination of gold(I) and enzyme catalysis is used in a two-step approach, including Meyer–Schuster rearrangement of a series of readily available propargylic alcohols followed by stereoselective bioreduction of the corresponding allylic ketone intermediates, to provide optically pure β,β-disubstituted allylic alcohols. This cascade involves a gold N-heterocyclic carbene and an enzyme, demonstrating the compatibility of both catalyst types in aqueous medium under mild reaction conditions. The combination of [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene][bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2) and a selective alcohol dehydrogenase (ADH-A from Rhodococcus ruber, KRED-P1-A12 or KRED-P3-G09) led to the synthesis of a series of optically active (E)-4-arylpent-3-en-2-ols in good yields (65–86 %). The approach was also extended to various 2-hetarylpent-3-yn-2-ol, hexynol, and butynol derivatives. The use of alcohol dehydrogenases of opposite selectivity led to the production of both allyl alcohol enantiomers (93->99 % ee) for a broad panel of substrates.
Copper(II)-Catalyzed Tandem Decarboxylative Michael/Aldol Reactions Leading to the Formation of Functionalized Cyclohexenones
Lee, Jeonghyo,Wang, Sibin,Callahan, Miranda,Nagorny, Pavel
, p. 2067 - 2070 (2018/04/16)
This work describes the development of a new single-pot copper(II)-catalyzed decarboxylative Michael reaction between β-keto acids and enones, followed by in situ aldolization, which results in highly functionalized chiral and achiral cyclohexenones. The achiral version of this Robinson annulation features a hitherto unprecedented Michael reaction of β-keto acids with sterically hindered β,β′-substituted enones and provides access to all carbon quaternary stereocenter-containing cyclohexenones (11 examples, 43-83% yield). In addition, an asymmetric chiral bis(oxazoline) copper(II)-catalyzed single-pot Robinson annulation has been devised for preparing chiral cyclohexenones, including some products that contain vicinal stereocenters (5 examples, 65-85% yield, 84-94% ee). This latter protocol has been successfully applied to the enantioselective formation of the oxygenated 10-nor-steroid core from readily available starting materials.
The synthesis of non-racemic β-alkyl-β-aryl-disubstituted allyl alcohols and their transformation into allylamines and amino acids bearing a quaternary stereocenter
Narczyk, Aleksandra,Pieczykolan, Micha?,Stecko, Sebastian
supporting information, p. 3921 - 3946 (2018/06/08)
A synthesis of non-racemic β-alkyl-β-aryl allyl alcohols and their transformation into allylamines bearing a quaternary stereogenic center is reported. The allyl alcohols were prepared either by Cu-catalyzed enantioselective reduction of enones or by sequ
Nickel-catalyzed cross-coupling of β-carbonyl alkenyl pivalates with arylzinc chlorides
Pan, Wen-Jing,Wang, Zhong-Xia
, p. 1029 - 1036 (2018/02/19)
The nickel-catalyzed cross-coupling reaction of β-carbonyl alkenyl pivalates with arylzinc reagents generates 3-aryl-substituted α,β-unsaturated carbonyl compounds via C-O bond cleavage. The reaction features mild reaction conditions, a wide scope of substrates, and good functional group tolerance.
Preparation and decarboxylative rearrangement of (Z)-enyne esters
Woo, Jacqueline C.S.,Walker, Shawn D.,Faul, Margaret M.
, p. 5679 - 5682 (2008/02/10)
A method to assemble (Z)-enyne esters via palladium-catalyzed cross coupling reactions of enol tosylates is reported. A base-mediated one-pot decarboxylative rearrangement of the enynes to enones is described. The scope of this process is examined.
REACTIONS OF ARYLAZO ARYL SULFONES WITH α,β-UNSATURATED ESTERS AND KETONES CATALYZED BY PALLADIUM(0) COMPLEX
Kamigata, Nobumasa,Satoh, Akira,Yoshida, Masato
, p. 121 - 130 (2007/10/02)
The palladium(0) catalyzed reactions of arylazo aryl sulfones (1) with α,β-unsaturated esters in benzene give aryl-substituted esters as major products and hydroarylated esters as minor products.The reactions of 1 with acyclic α,β-unsaturated ketones give considerable amounts of hydroarylated ketones and aryl-substituted ketones under similar conditions, whereas the reactions of 1 with cyclic α,β-unsaturated ketones afforded selectively hydroarylated compounds and no formation of aryl-substituted ketones was found.A plausible reaction mechanism is proposed.Key words: Arylazo aryl sulfones; palladium(0) catalyst; arylation; α,β-unsaturated carbonyl compounds; diarylpalladiumII) intermediate; catalytic cycle.
Reaction of 6-Methyl-6-p-tolyl-4-ethoxy-5,6-dihydro-pyran-2-one with Perchloric Acid
Anand, R. C.,Ranjan,H.
, p. 1343 - 1346 (2007/10/02)
6-Methyl-6-p-tolyl-4-ethoxy-5,6-dihydro-pyran-2-one(1) undergoes decarboxylative elimination with perchloric acid in ether to give 4-p-tolyl-3-penten-2-one(3), the structure of which has been confirmed through an unambiguous synthesis. - Keywords: Decarboxylative elimination, β-Keto-δ-lactone
