133128-40-2

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 98-09-9 benzenesulfonyl chloride 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 882-33-7 diphenyldisulfane 
• 35998-30-2 3-(phenylsulfanyl)-3,4-dihydrofuran-2-one 
• 130307-35-6 3-(phenylthio)-4,5-dihydrofuran 
• 72842-31-0 3-benzenesulfonyl-dihydro-furan-2-one 

Downstream Products

• 260364-26-9 (4R,5R,7R,8R,9R,10R)-7,8-O-(di-tert-butylsilylene)-8,9,10-trihydroxy-7-hydroxymethyl-4-phenylsulfonyl-9-O-(trimethylsilyl)-1,6-dioxaspiro[4.5]decane 
• 260364-27-0 (4R,5R,7R,8R,9R,10R)-7,8-O-(di-tert-butylsilylene)-8,9,10-trihydroxy-7-hydroxymethyl-4-phenylsulfonyl-1,6-dioxaspiro[4.5]decane 
• 260364-25-8 (4R,5R,7R,8R,9S)-7,8-O-(di-tert-butylsilylene)-8,9-dihydroxy-7-hydroxymethyl-4-phenylsulfonyl-9-O-(trimethylsilyl)-1,6-dioxaspiro[4.5]decan-10-one 

Relevant academic research and scientific papers

Synthesis of vinyl sulfoxides using sulfinyl chlorides and olefins

A general method for synthesis of vinyl sulfoxides, using sulfinyl chlorides and olefins as starting materials and DBU as an HCl scavenger, has been developed. Vinyl sulfoxides were obtained from the ZnCl2 catalysed addition of sulfinyl chlorides to olefins followed by the elimination with DBU. However, the direct reaction of sulfinyl chlorides with olefins in the presence of DBU, usually leads to generation of vinyl sulfones. The sulfonyl radicals generated from the DBU-mediated disproportionation of the sulfinyl radicals undergo addition-elimination reaction with olefins to give vinyl sulfones.

New approach to the stereoselective synthesis of the [4.5] spiroketal moiety of papulacandins

An efficient approach for the stereoselective construction of the spiroketal moiety of papulacandins, based on the condensation of the protected derivative of D-arabino-1,4-lactone 2 with the α-lithiated carbanion of β-phenylsulfonyl dihydrofuran 1, is de

Second Generation Doetz Benzannulation Reactions in Organic Synthesis

A modified Doetz benzannulation reaction has been developed for the synthesis of benzofuran derivatives.

New one-step process for the synthesis of functionalized 1,6-dioxaspiro[4,5]decanes

β-Phenylsulfonyl dihydrofurans 1 were readily prepared by reduction of α-phenylsulfonyl-γ-lactones with DIBAL-H, followed by dehydration with MsCl-Et3N. Dihydrofurans 1 were deprotonated with n-BuLi and the resulting α-lithiated carbanion reacted with a wide variety of electrophiles. Particularly interesting is its reaction with γ-lactones because it affords 1,6-dioxaspiro[4,5]decanes in good yields in one-step procedure. This new method of synthesis of spiroketals, in non-acid conditions, is thermodynamically controlled and occurs with high stereoselectivity at C-4, C-5 and C-7, but not at C-2.

One-step Synthesis of Functionalized Dioxaspirodecanes from β-Phenylsulfonyl Dihydrofurans and γ-Lactones

A one-step synthesis of differently substituted 1,6-dioxaspirodecanes from readily available starting materials is described.The process is based on the condensation of the α-anion derived from β-phenylsulfonyl dihydrofurans with γ-lactones.The spirocyclization occurs with high stereoselectivity at C-4, C-5 and C-9, but not at C-2.

Generation of [β-(phenylsulfonyl)alkylidene]carbenes from hypervalent alkenyl- and alkynyliodonium tetrafluoroborates and synthesis of 1-(phenylsulfonyl)cyclopentenes

Michael-type addition of benzenesulfinic acid to alkynyl(phenyl)iodonium tetrafluoroborates in methanol gives stereoselectively (Z)-(β-(phenylsulfonyl)alkenyl)iodonium tetrafluoroborates in high yields. [β-(Phenylsulfonyl)alkylidene]carbenes derived from