777-93-5Relevant academic research and scientific papers
Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids
Duhamel, Thomas,Mu?iz, Kilian
, p. 933 - 936 (2019/01/23)
A new method for the formation of γ- and δ-lactones from carboxylic acids through direct conversion of benzylic C-H to C-O bonds is described. The reaction is conveniently induced by visible light and relies on a mild cooperative catalysis by the combination of molecular iodine and an organic dye.
Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations
Betori, Rick C.,May, Catherine M.,Scheidt, Karl A.
, p. 16490 - 16494 (2019/11/03)
Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.
Pd-Catalyzed reductive heck reaction of olefins with aryl bromides for Csp2-Csp3 bond formation
Jin, Liqun,Qian, Jiaxia,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
supporting information, p. 5752 - 5755 (2018/06/07)
We developed a Pd-catalyzed intermolecular reductive Heck reaction to construct Csp2-Csp3 bonds between aryl bromides and olefins. Various styrene derivatives, acyclic and cyclic alkenes, were well tolerated to couple with varied aryl bromides in linear selectivity. Kinetic and deuterium labeling experiments suggested that i-PrOH provides a hydride through β-H elimination.
Iridium/f-Amphol-catalyzed Efficient Asymmetric Hydrogenation of Benzo-fused Cyclic Ketones
Yin, Congcong,Dong, Xiu-Qin,Zhang, Xumu
, p. 4319 - 4324 (2018/10/15)
Iridium/f-Amphol-catalyzed asymmetric hydrogenation of various benzo-fused five to seven-membered cyclic ketones was successfully developed, affording a series of chiral benzo-fused cyclic alcohols with excellent results (75%–99% yields, 93%–>99% ee, and TON up to 297 000). The enantioenriched products can be employed as key intermediates or motifs for the synthesis of some important biologically active compounds, such as rasagiline mesylate TVP-1012 used for the treatment of Parkinson's disease, the enantiomer of anticonvulsant drug eslicarbazepine acetate (BIA 2-093). (Figure presented.).
Synthesis of (3S)-(tert-butyldimethylsilyloxy)methylcyclopentan-1-one as a key intermediate of sphingosine 1-phosphate-1 receptor agonists
Asano, Masayoshi,Nakamura, Tsuyoshi,Sekiguchi, Yukiko,Mizuno, Yumiko,Yamaguchi, Takahiro,Kuroda, Takeshi,Tamaki, Kazuhiko,Nishi, Takahide
, p. 449 - 456 (2013/07/11)
Herein we report the asymmetric synthesis of (3S)-(tert- butyldimethylsilyloxy)methylcyclopentan-1-one (S)-3 as a practical chiral synthon for a wide range of pharmaceutical and/or natural products, using Lipshutz's asymmetric copper-catalyzed conjugate reduction. This method makes it feasible to prepare a conformationally constrained cyclopentane analogue 12, which is one of the key intermediates for the synthesis of novel sphingosine 1-phosphate-1 receptor agonists.
Synthesis and cross-coupling reactions of solid-supported alkylzinc reagents
Jackson, Richard F. W.,Oates, Leslie J.,Block, Michael H.
, p. 1401 - 1402 (2007/10/03)
Hydroboration of Wang-supported pent-4-enoic acid 1, followed by transmetallation with Et2Zn, gives a solid-supported zinc reagent, 2, which undergoes palladium-catalysed coupling with aryl iodides, to give the corresponding 5-arylpentanoic acids 3 in moderate to good yields, after cleavage from the resin using TFA.
