Stereoselective synthesis of hydroxy stilbenoids and styrenes by atom-efficient olefination with thiophthalides
The synthesis of stilbenoids and styryl carboxylic acids is accomplished with high E-stereoselectivity by olefination of aldehydes with thiophthalides under basic conditions. The olefination is highly atom-efficient as it only loses elemental sulfur during the reaction. This olefination, in conjunction with retro Kolbe-Schmitt reaction, allows facile synthesis of E-hydroxystilbenoids with minimal employment of protecting groups. This study also discloses two important findings: formation of i) 4-methylsulfanyl isocoumarins and ii) an 2-arylindenone. The Royal Society of Chemistry 2012.
Mitra, Prithiba,Shome, Brateen,Ranjan De, Saroj,Sarkar, Anindya,Mal, Dipakranjan
p. 2742 - 2752
(2012/11/07)
Stereospecific Formation of 2-benzoic Acids in an Unusual Reaction of Thiophthalides with Aldehydes
The reaction of thiophthalides 1 with aldehydes 3 in the presence of lithium tert-butoxide at -60 deg C to 25 deg C results in the stereospecific formation of only trans 2-(alk-1'-enyl)benzoic acids 4 in fairly good yields in one-pot operations.This react
Mal, Dipakranjan,Majumdar, Gita,Pal, Ranjan
p. 1115 - 1116
(2007/10/02)
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