150192-39-5Relevant articles and documents
A Chan-Evans-Lam approach to trisubstituted vinyl ethers
Molder, Bryce A.,Sader, Jonathan K.,Wulff, Jeremy E.
supporting information, p. 9649 - 9653 (2021/12/01)
Trisubstituted vinyl ethers were accessedviaChan-Evans-Lam coupling of vinyl trifluoroborates and primary aliphatic alcohols. This approach complements prior methods that required the use of neat liquid alcohol coupling partners. A palladium-catalyzed redox-relay Heck reaction was used to convert several vinyl ethers into aldehyde-functionalized 1,3-dihydroisobenzofurans.
Catalytic Cyclotrimerization Pathway for Synthesis of Selaginpulvilins C and D: Scope and Limitations
Rycek, Lukas,Mateus, Miguel,Beytlerová, Nela,Kotora, Martin
supporting information, p. 4511 - 4515 (2021/04/12)
A facile and unified approach to the main selaginpulvilin's framework was achieved by catalytic [2 + 2 + 2]-cyclotrimerization of a triyne with monosubtituted alkynes. The reaction proceeded with high "ortho"selectivity by using Wilkinson's catalyst (RhCl
Regiocontrolled and Stereoselective Syntheses of Tetrahydrophthalazine Derivatives using Radical Cyclizations
Zhang, Wei,Mo, Jia Yi,He, Weiying,Kennepohl, Pierre,Sammis, Glenn M.
supporting information, p. 976 - 980 (2019/01/04)
Tetrahydrophthalazine derivatives have found important applications in pharmaceutical research, but existing synthetic methods are unable to access them regio- and stereoselectively. Here, a new approach is presented that addresses these challenges by utilizing a 6-endo-trig radical cyclization in the key step. The desired tetrahydrophthalazines can be accessed in high yields (55–98 %) and high diastereoselectivities for the trans-product (>95:5) starting either from readily accessible hydrazones, or from the corresponding aldehydes and substituted Boc-hydrazides in a one-pot process. The synthetic versatility of the tetrahydrophthalazine core was demonstrated by its straightforward conversion to dihydro-phthalazines, phthalazines, or pyrazolo dione derivatives. Furthermore, the N?N bond was reduced to afford a new route to 1,4-diamines.
Metal- and Hydride-Free Pentannulative Reductive Aldol Reaction
Satpathi, Bishnupada,Dutta, Lona,Ramasastry
supporting information, p. 170 - 174 (2019/01/04)
Traditionally, the reductive aldol reaction is a metal-catalyzed and hydride-promoted coupling between enones and aldehydes. We present a phosphine-mediated diastereoselective intramolecular reductive aldol reaction of α-substituted dienones and aldehydes, which is metal-free and hydride-free. The synthetic utility of the reductive aldol adducts is demonstrated by elaborating them in one step to indeno[1,2-b]furanones, indeno[1,2-b]pyrans, and dibenzo[a,h]azulen-8-ones.
Stereoselective Convergent Synthesis of Tetrahydro-5 H-benzo[c]fluorene via Nine-Membered Ring-Closing Metathesis and Transannular Acid-Mediated Cyclization/Nucleophilic Addition
Lekky, Anek,Ruengsatra, Tanachote,Ruchirawat, Somsak,Ploypradith, Poonsakdi
, p. 5277 - 5291 (2019/05/10)
The diene methyl ethers or acetates, constructed from the Li-Br exchange/addition reactions of 2-vinylbenzaldehydes and 2-(but-3-en-1-yl)bromoarenes followed by etherification or acetylation of the corresponding alcohols, smoothly underwent the ring-closi
Rh(III)-Catalyzed Phosphine Oxide Migration Reactions: Selective Synthesis of 3-Phosphinoylindoles
Wang, Chun-Hai,Yang, Shang-Dong
supporting information, p. 2401 - 2404 (2018/09/10)
3-Phosphinoylindoles are important components of biological active natural products and materials in pharmaceuticals. Herein, a new approach for the synthesis of 3-phosphinoylindoles has been established by a Rh(III)-catalyzed cyclization from readily acc
Methanol as hydrogen source: Transfer hydrogenation of aromatic aldehydes with a rhodacycle
Aboo, Ahmed H.,Bennett, Elliot L.,Deeprose, Mark,Robertson, Craig M.,Iggo, Jonathan A.,Xiao, Jianliang
supporting information, p. 11805 - 11808 (2018/11/10)
A cyclometalated rhodium complex has been shown to perform highly selective and efficient reduction of aldehydes, deriving the hydrogen from methanol. With methanol as both the solvent and hydrogen donor under mild conditions and an open atmosphere, a wide range of aromatic aldehydes were reduced to the corresponding alcohols, without affecting other functional groups.
Deconjugative alkylation/Heck reaction as a simple platform for dihydronaphthalene synthesis
Navaratne, Primali V.,Grenning, Alexander J.
supporting information, p. 69 - 75 (2016/12/27)
A simple platform for carbocycle synthesis by Knoevenagel adduct deconjugative alkylation/Heck reaction is described. Deconjugative alkylation of Knoevenagels adducts is two-fold synthetically enabling because C-C bond formation is (1) operationally simple due to the ease of Knoevenagel adduct carbanion generation and (2) results in alkene migration, which poises the substrate for cyclization. Furthermore, the gem-dinitrile moiety serves as a functional group for synthetic manipulation.
An enantioselective organocatalytic intramolecular Morita-Baylis-Hillman (IMBH) reaction of dienones, and elaboration of the IMBH adducts to fluorenones
Satpathi, Bishnupada,Wagulde, Siddhant V.,Ramasastry
supporting information, p. 8042 - 8045 (2017/07/22)
An enantioselective organocatalytic intramolecular Morita-Baylis-Hillman (IMBH) reaction of dienones is reported for the first time. This has been achieved by incorporating entropy and synergy considerations during the substrate design. The reaction conditions are thoroughly verified for an efficient synthesis of highly functionalised cyclopenta-fused arenes and heteroarenes in excellent yields and enantioselectivities. The synthetic utility of the IMBH-adducts has been demonstrated by transforming them into 3,4-disubstituted fluorenones in a serendipitous manner.
Morita-Baylis-Hillman Reaction of β,β-Disubstituted Enones: An Enantioselective Organocatalytic Approach for the Synthesis of Cyclopenta[b]annulated Arenes and Heteroarenes
Satpathi, Bishnupada,Ramasastry
supporting information, p. 1777 - 1781 (2016/02/03)
The first enantioselective organocatalytic intramolecular Morita-Baylis-Hillman (MBH) reaction of sterically highly demanding β,β-disubstituted enones is presented. The MBH reaction of β,β-disubstituted-α,β-unsaturated electron-withdrawing systems was previously considered to be unfeasible. Towards this end, designer substrates, which under simple and practical reaction conditions generate a variety of cyclopenta[b]annulated arenes and heteroarenes in excellent enantiopurities and near-quantitative yields in remarkably short reaction times, are described. The reason for the unusually facile nature of this reaction is attributed to the synergy guided and entropically favored intramolecular reaction. Further, this strategy provides easy access to a substantial number of bioactive natural products and pharmaceutically significant compounds.