1245945-55-4Relevant academic research and scientific papers
Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis
Pandey, Ganesh,Laha, Ramkrishna,Mondal, Pradip Kumar
supporting information, p. 9689 - 9692 (2019/08/15)
A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (-)-codonopsinine and (+)-centrolobine. Herein it is proposed that selectfluor, unlike a fluorinating reagent, acts as an oxidative quencher and a hydrogen radical acceptor.
Structure-activity relationship for thiirane-based gelatinase inhibitors
Lee, Mijoon,Ikejiri, Masahiro,Klimpel, Dennis,Toth, Marta,Espahbodi, Mana,Hesek, Dusan,Forbes, Christopher,Kumarasiri, Malika,Noll, Bruce C.,Chang, Mayland,Mobashery, Shahriar
supporting information; experimental part, p. 490 - 495 (2012/08/14)
An extensive structure-activity relationship study with the template of 2-(4-phenoxyphenylsulfonylmethyl)thiirane (1), a potent and highly selective inhibitor for human gelatinases, is reported herein. Syntheses of 65 new analogues, each in multistep processes, allowed for exploration of key structural components of the molecular template. This study reveals that the presence of the sulfonylmethylthiirane and the phenoxyphenyl group were important for gelatinase inhibition. However, para- and some meta-substitutions of the terminal phenyl ring enhanced inhibitory activity and led to improve metabolic stability. This agrees with the result from metabolism studies with compound 1 that the primary route of biotransformation is oxidation, mainly at the para position of the phenyl ring and the α position of the sulfonyl group in the aliphatic side chain.
The catalyzed desulfinylative allylation of carbonyl compounds with alk-2-enesulfonyl chlorides and silyl alk-2-enesulfinates
Volla, Chandra M. R.,Markovic, Dean,Laclef, Sylvain,Vogel, Pierre
supporting information; experimental part, p. 8984 - 8988 (2010/10/02)
Coupling up with sulfonyl chlorides: An ene reaction of alkenes with SO2·BCl3 permits the one-pot conversion of simple alkenes into b,g-unsaturated sulfonyl chlorides or sulfinic silyl esters. These compounds can then be used as nucleophilic allylating agents with aldehydes and ketones to generate the corresponding homoallylic alcohols (see scheme) with good chemo-and diastereoselectivity in the presence of a suitable catalyst and reducing agent.
