61783-64-0

Upstream product

• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 693-02-7 hex-1-yne 
• 32359-01-6 hexenylmagnesium bromide 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 98147-48-9 2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate 

Downstream Products

• 99930-89-9 (Z)-2-methyl-1-hexenyl p-tolyl (-)-(R)-sulfoxide 
• 158414-03-0 (S)-2-Butyl-3-((S)-toluene-4-sulfinyl)-4,5,6,7-tetrahydro-3aH-isoxazolo[2,3-a]pyridine 
• 157070-37-6 (R)-2-Butyl-3-((S)-toluene-4-sulfinyl)-4,5,6,7-tetrahydro-3aH-isoxazolo[2,3-a]pyridine 
• 205251-15-6 (Z)-2-n-butyl-3-[(R)-p-tolylsulfinyl]propenonitrile 
• 397244-53-0 (1E,SS)-(-)-2-(p-chlorophenyl)-1-hexenyl p-tolyl sulfoxide 
• 612065-40-4 (αR)-α-[(1R)-1-ethyl-1-[1-[(S)-(4-methylphenyl)sulfinyl]ethenyl]pentyl]-benzenemethanol 
• 817160-97-7 (E)-4-butyl-5-[(R)-(p-tolyl)sulfinyl]-4-pentenyl pivalate 

Relevant academic research and scientific papers

Synthesis of Enantiopure 3-Hydroxypiperidines from Sulfinyl Dienyl Amines by Diastereoselective Intramolecular Cyclization and [2,3]-Sigmatropic Rearrangement

The highly diastereoselective base-promoted intramolecular cyclization of a variety of enantiopure sulfinyl dienyl amines provides novel sulfinyl tetrahydropyridines that are readily converted to 3-hydroxy tetrahydropyridines via sigmatropic rearrangement. The influence of N- and C- substituents on the process has been studied. Procedures to shorten the sequence such as the tandem cyclization followed by [2,3]-sigmatropic rearrangement, as well as cyclization of the free amine, under Boc- or ArSO- deprotection conditions have been examined. Good to excellent levels of selectivity are generally observed for the reported transformations (dr: 75/25 to >98/2). A novel protocol to access substituted amino dienyl sulfoxides is also reported.

First Highly Stereoselective Synthesis of Fungicide Systhane

Highly enantiopure (R)-2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile 1 (myclobutanil or systhane) was obtained in six synthetic steps from commercially available 1-hexyne (35% yield, 92% ee). The sulfinyl group controls the two key steps o

(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.

Simple and Stereocontrolled Preparation of Optically Pure (E)- and (Z)-1-Alkenyl p-Tolyl Sulfoxides via 1-Alkynyl p-Tolyl Sulfoxides

1-Alkynylmagnesium bromides react cleanly and stereospecifically with (-)-menthyl (-)-(S)-p-toluenesulfinate (2) in toluene to produce chiral 1-alkynyl p-tolyl (+)-(S)-sulfoxides 5a-d in high yields.Reduction of 5a-d with lithium aluminum hydride in THF a

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