99930-83-3

Upstream product

• 61210-52-4 (trimethylsilyl)ethynylmagnesium bromide 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 99930-84-4 Trimethyl-((S)-toluene-4-sulfinylethynyl)-silane 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 4301-14-8 acetylenemagnesium bromide 
• 98147-48-9 2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate 
• 74-86-2 acetylene 

Downstream Products

• 118089-99-9 (-)-(S)_S-p-tolylsulfinyl-2<1S,4R>bicyclo<2.2.1>heptadiene-2,5 
• 118089-98-8 (+)-(S)-p-tolylsulfinyl-2<1R,4S>bicyclo<2.2.1>heptadiene-2,5 
• 123975-84-8 (-)-(R)_S-p-tolylsulfinyl-1 cyclohexadiene-1,4 
• 128534-66-7 (-)-(R)_S-dimethyl-4,5 p-tolylsulfinyl-1 cyclohexadiene-1,4 
• 127418-20-6 (-)-(R)_S-methyl-5 p-tolylsulfinyl-1 cyclohexadiene-1,4 
• 127418-19-3 (-)-(R)_S-methyl-4 p-tolylsulfinyl-1 cyclohexadiene-1,4 
• 205251-17-8 (Z)-3-[(R)-p-tolylsulfinyl]propenonitrile 
• 18937-82-1 undeca-5,6-diene 
• 18937-82-1 1,3-Di-n-butylallen 
• 862603-61-0 Toluene-4-sulfonic acid (S)-3-((2S,4S)-2-phenyl-[1,3]dioxan-4-yl)-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester 
• 862603-02-9 Toluene-4-sulfonic acid (S)-3-{(2S,5R)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-tetrahydro-furan-2-yl}-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester 
• 949932-63-2 C₁₃H₁₈O₃S 
• 949932-64-3 C₁₃H₁₈O₃S 
• 949932-71-2 C₂₇H₄₀O₄SiS 

Relevant academic research and scientific papers

New multicomponent approach for the creation of chiral quaternary centers in the carbonyl allylation reactions

The combined regio- and stereo-controlled carbometalation reaction of alkynyl sulfoxide followed by a zinc homologation and finally an allylation reaction led, in a single-pot operation, to chiral homoallylic alcohols in excellent yields and diastereosele

(Z)-3-p-tolylsulfinylacrylonitriles as chiral dipolarophiles: Reactions with diazoalkanes

(figure presented) The dipolarophilic reactivity of enantiopure (Z)-3-p-tolylsulfinylacrylonitriles (1) has been evaluated with diazoalkanes. 3-Cyanopyrazoles are obtained when R = H, but with R = alkyl (Bn, n-Bu, and t-Bu) only one cycloadduct (4 or 5) is formed in high yield under mild conditions, therefore evidencing a complete control of the regioselectivity and the endolexo and π-facial selectivities. These reactions are a new straightforward entry to the synthesis of pyrazolines and related structures and reveal the excellent dipolarophilic features of (Z)-sulfinylacrylonitriles.

Chiral Acetylenic Sulfoxide in Enantioselective Synthesis of Tetrahydroisoquinoline and Tetrahydro-β-carboline Alkaloids. Total Synthesis of (R)-(+)-Carnegine and (R)-(+)-Tetrahydroharman

Michael addition of 2-(3,4-dimethoxyphenyl)ethylamine 3 or tryptamine 4 onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded the basic alkaloid skeleton of tetraisoquinoline and tetrahydro-β-carboline in high to moderate diastereoselectivity.Optically pure (R)-(+)-carnegine and (R)-(+)-tetrahydroharman have been synthesized.

Chiral acetylenic sulfoxide in alkaloid synthesis. Total synthesis of (R)-(+)-carnegine

Remarkable diastereoselectivity was observed in the cyclization of β-aminovinyl sulfoxide 5a prepared from chiral acetylenic sulfoxide 1a in acidic medium. The cyclized product 6a was then converted to (R)-(+)-carnegine.

A SIMPLE PREPARATIVE METHOD FOR OPTICALLY PURE 1-ALKENYL p-TOLYL SULFOXIDES VIA 1-ALKYNYL p-TOLYL SULFOXIDES

1-Alkynyl Grignard reagents react with (SS)-(-)-menthyl p-toluene-sulfinate in toluene to give optically active 1-alkynyl p-tolyl sulfoxides in high yields.The 1-alkynyl sulfoxides thus obtained undergo a stereoselective hydroalumination follow