7397-10-6Relevant academic research and scientific papers
Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives
Kearney, Aoife M.,Murphy, Linda,Murphy, Chloe C.,Eccles, Kevin S.,Lawrence, Simon E.,Collins, Stuart G.,Maguire, Anita R.
supporting information, (2021/05/04)
The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.
Tandem Pd/Au-catalyzed route to α-sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols
Biswas, Srijit,Watile, Rahul A.,Samec, Joseph S. M.
supporting information, p. 2159 - 2163 (2014/03/21)
An efficient and highly atom-economical tandem Pd/Au-catalyzed route to α-sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols has been developed. This one-step procedure has a wide substrate scope with respect to substituents at
PREPARATION OF [ALPHA]-SULFENYLATED CARBONYL COMPOUNDS FROM PROPARGYLIC ALCOHOLS IN ONE STEP
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Page/Page column 13-14, (2013/08/15)
The present relates to a method and a kit to produce an optically pure α-sulfenylated carbonyl compound comprising a primary or a secondary propargylic alcohol and an aryl thiol, a transition metal catalyst and a solvent.
A new method for stereocontrolled synthesis of substituted tetrahydrothiophenes
Ponce, Andres Molina,Overman, Larry E.
, p. 8672 - 8676 (2007/10/03)
A variety of substituted 3-acyltetrahydrothiophenes can be prepared with high stereoselectivity in 50-70% yield by acid-promoted condensation of mercapto allylic alcohols 1 (X = S) with aldehydes and ketones. The mercapto allylic alcohol must be substitut
α-Thio-substituted Ketones as Precursors of Olefins via Oxathiolanes: Benzyl as Protecting Group
Brown, Michael D.,Whitham, Gordon H.
, p. 817 - 822 (2007/10/02)
The feasibility of a regiospecific synthesis of tetrasubsituted olefins starting from protected α-thiol substituted ketones has been demonstrated by three examples.The approach (see Scheme) involves: S-activated alkylation (i), carbonyl addition of an organometallic reagent (ii), deprotection (iii), formation of a 2-phenyloxathiolane (iv), and base-promoted cycloelimination (v).An unsatisfactory feature is the lack of stereochemical control in step (ii).An attempt to telescope steps (iii) and (iv) by sequential Pummerer reaction-cyclisation at the β-benzylthio alcohol stage was unsuccessful.
