80398-84-1Relevant academic research and scientific papers
Divergent Synthesis of Cyclopropane-Containing Lead-Like Compounds, Fragments and Building Blocks through a Cobalt Catalyzed Cyclopropanation of Phenyl Vinyl Sulfide
Chawner, Stephen J.,Cases-Thomas, Manuel J.,Bull, James A.
, p. 5015 - 5024 (2017/09/22)
Cyclopropanes provide important design elements in medicinal chemistry and are widely present in drug compounds. Here we describe a strategy and extensive synthetic studies for the preparation of a diverse collection of cyclopropane-containing lead-like compounds, fragments and building blocks exploiting a single precursor. The bifunctional cyclopropane (E/Z)-ethyl 2-(phenylsulfanyl)-cyclopropane-1-carboxylate was designed to allow derivatization through the ester and sulfide functionalities to topologically varied compounds designed to fit in desirable chemical space for drug discovery. A cobalt-catalyzed cyclopropanation of phenyl vinyl sulfide affords these scaffolds on multigram scale. Divergent, orthogonal derivatization is achieved through hydrolysis, reduction, amidation and oxidation reactions as well as sulfoxide–magnesium exchange/functionalization. The cyclopropyl Grignard reagent formed from sulfoxide exchange is stable at 0 °C for > 2 h, which enables trapping with various electrophiles and Pd-catalyzed Negishi cross-coupling reactions. The library prepared, as well as a further virtual elaboration, is analyzed against parameters of lipophilicity (ALog P), MW and molecular shape by using the LLAMA (Lead-Likeness and Molecular Analysis) software, to illustrate the success in generating lead-like compounds and fragments.
STRAIN AND SELECTIVITY: PARTNERS FOR ORGANIC SYNTHESIS
Trost, Barry M.
, p. 139 - 150 (2007/10/02)
The development of two new small-ring conjunctive reagents, (E)-2-(hydrohymethyl)cyclopropyl phenyl sulphide and 1,1-bis(benzenesulphonyl)cyclopropane, are reported.The former permits a synthesis of 2,4-disubstituted cyclobutanones and (E)-4-phenylthio-4-
Bifunctional Cyclopropyl Reagents: Stereocontrolled Approach to Vinyl Sulfides and Chemodifferentiated 1,4-Dicarbonyl Systems
Trost, Barry M.,Ornstein, Paul L.
, p. 748 - 751 (2007/10/02)
The use of (E)-2-(hydroxymethyl)cyclopropyl phenyl sulfide as a useful conjunctive reagent, particularly in a stereocontrolled synthesis of vinyl sulfides, is reported.
A CHEMOSELECTIVE DESULFURIZATION METHOD VIA HOMOGENEOUS NICKEL CATALYSIS
Trost, Barry M.,Ornstein, Paul L.
, p. 3463 - 3466 (2007/10/02)
Isopropylmagnesium bromide in the presence of bis-(triphenylphosphino)-nickel(II) chloride reduces vinyl sulfides stereospecifically to the corresponding olefins without overreduction - a process which serves as a key step in the synthesis of the sex pheromone of the Douglas fir tussock moth.
