31350-93-3

Upstream product

• 622-63-9 ethyl p-tolyl sulfide 
• 6378-07-0 ethyl (p-tolyl)sulfoxide 
• 1519-40-0 (+)-(R)-ethyl p-tolyl sulfoxide 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 106-45-6 para-thiocresol 
• 62961-00-6 (S)-1-(ethylsulfinyl)-4-methylbenzene 
• 10467-10-4 ethylmagnesium iodide 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 

Downstream Products

• 134970-66-4 4-Chloro-1-phenyl-4-(toluene-4-sulfinyl)-pentan-3-ol 
• 134970-38-0 8-[1-Chloro-1-(toluene-4-sulfinyl)-ethyl]-1,4-dioxa-spiro[4.5]decan-8-ol 
• 159763-14-1 1-<1-chloro-1-(p-tolylsulfinyl)ethyl>-1-cyclooctanol 
• 119487-82-0 [(1S,2S)-2-Chloro-1-phenyl-2-(toluene-4-sulfinyl)-propyl]-phenyl-amine 
• 119487-82-0 [(1S,2S)-2-Chloro-1-phenyl-2-((S)-toluene-4-sulfinyl)-propyl]-phenyl-amine 
• 159763-13-0 1-<1-chloro-1-(p-tolylsulfinyl)ethyl>-4-tert-butyl-1-cyclohexanol 
• 159763-15-2 1-<1-chloro-1-(p-tolylsulfinyl)ethyl>-1-cyclododecanol 
• 119507-88-9 [(1S,2S)-2-Chloro-1-(4-chloro-phenyl)-2-(toluene-4-sulfinyl)-propyl]-phenyl-amine 
• 119507-88-9 [(1S,2S)-2-Chloro-1-(4-chloro-phenyl)-2-((S)-toluene-4-sulfinyl)-propyl]-phenyl-amine 
• 134970-67-5 2-Chloro-1-cyclohexyl-2-(toluene-4-sulfinyl)-propan-1-ol 
• 134970-37-9 1-[1-Chloro-1-(toluene-4-sulfinyl)-ethyl]-cycloheptanol 
• 119487-86-4 (E)-2-methyl-1,3-diphenyl-2-(p-tolylsulfinyl)aziridine 
• 733016-26-7 1-[1-chloro-1-(p-tolylsulfinyl)ethyl]-1-cyclopentadecanol 

Relevant academic research and scientific papers

Chain Extension of Boronic Esters with Lithiooxiranes Generated by Sulfoxide-Metal Exchange - Stereocontrolled Access to 2°/2°, 2°/3°, and 3°/3° Vicinal Diols and Related Compounds

Lithiooxiranes [LiCR1(O)CR2R3, R1 = H, Me; R2/R3 = H/Ph, H/tBu, Me/Ph], generated by sulfoxide-lithium exchange from stereodefined sulfinyl epoxides (with use of PhLi or tBuLi, THF, at or below -90 °C), were employed for the stereospecific reagent-controlled homologation of boronic esters R0-Bpin (R0 = BnCH2, allyl, cHex, Ph). Addition of TBSOTf to the intermediate ate complexes gave β-silyloxyboronates that were converted to vicinal diol monosilyl ethers by oxidative work-up with aq. NaOOH. The 2°/2° (4-32 %, dr > 98:2), 2°/3° (21-66 %, dr ≥ 65:35), and 3°/3° (59-68 %, dr ≥ 95:5) contiguous stereodiad-containing compounds created in this manner were typically obtained in a highly stereocontrolled manner. In general, cis-sulfinyl epoxides afforded anti-like stereodiads, whereas trans-sulfinyl epoxides afforded syn-like stereodiads; however, as a result of its suspected configurational instability, LiCMe(O)CHPh gave anti-like 2°/3° motifs regardless of sulfinyl epoxide stereochemistry.

Stereoselective preparation of (E)-configured 1,2-disubstituted propenes from two aldehydes by a two-carbon stitching strategy: Convergent synthesis of 18,21-diisopropyl-geldanamycin hydroquinone and its C7 epimer

The title compounds were synthesized in a longest sequence of 27 linear steps and with an overall yield of 2.9 and 3.9 %. In the course of the synthesis, two aldehydes representing carbon fragments C1-C7 (Eastern fragment) and C9-C21 (Western fragment) were prepared from D-mannitol, each of which incorporated a key stereogenic center at the respective secondary methyl ether group (C6, C12) from the chiral pool material. The assembly of the two aldehydes was achieved employing α-chloroethyl magnesium chloride as a two-carbon building block. The carbenoid reagent was generated from α-chloroethyl para-tolylsulfoxide by sulfoxide-magnesium exchange and it added smoothly to the highly sensitive aldehyde of the Eastern fragment (C1-C7). Upon oxidation, an α-chloroethyl ketone was generated, which underwent a clean and high-yielding reductive SmI2-promoted addition to the other aldehyde fragment. Dehydration delivered the key double bond between C8 and C9 in an overall yield of 72 % over four steps. The method was shown to be generally applicable to the racemization-free conversion of several aldehydes into the respective α-chloroethyl ketone (11 examples, 64-95 %) and to the coupling protocol (5 examples, 66-90 %). The further course of the geldanamycin hydroquinone synthesis included a diastereoselective reduction at C7 and the implementation of the amino group at C20. Since deprotection of the two isopropyl protecting groups could not be achieved in significant yields, the structure of 18,21-diisopropyl-geldanamycin hydroquinone was proven by its independent synthesis from the natural product. Convergency in the synthesis of the geldanamycin skeleton has been achieved by employing a magnesium carbenoid as a two-carbon building block, connecting two aldehyde fragments in an efficient and high yielding manner. The preparation of α-chloroethyl ketones from aldehydes has been investigated (11 examples, 64-95 % yield) and the title compounds have been prepared from advanced precursor 1. Copyright

Novel synthesis of optically active 2-ethylhexanoic acid, 2-ethylhexanol, and 2-ethylhexylamine via the asymmetric favorskii rearrangement

The asymmetric Favorskii rearrangement of optically active α-haloketones, which are easily prepared from chiral menthyl-4- toluenesulfoxide in several steps using primary or secondary amines, yields their corresponding secondary or tertiary chiral amides.

Facile one-pot synthesis of α-chloro sulfoxides from sulfides

Various sulfides 1 reacted with sulfuryl chloride in the presence of metal nitrates in acetonitrile under mild conditions to give the corresponding α-chloro sulfoxides 2 in good yields.

Facile Synthesis of α-Chlorosulfoxide Using the N,N'-Dichloro-p-toluenesulfonamide

Various unsymmetrical and symmetrical dialkyl sulfoxides or alkyl aryl sulfoxides reacted with N,N'-dichloro-p-toluenesulfonamide to yield the corresponding α-chlorosulfoxide in excellent yields under mild and neutral conditions in high regioselectivity of monochlorination at α-position of sulfoxides.

A Novel Approach to the Asymmetric Synthesis of Epoxides, Allylic Alcohols, α-Amino Ketones, and α-Amino Aldehydes from Carbonyl Compounds through α,β-Epoxy Sulfoxides Using the Optically Active p-Tolylsulfinyl Group To Induce Chirality

A practical and relatively inexpensive procedure for the preparation of (-)-chloromethyl p-tolyl sulfoxide of high optical purity was accomplished by the chlorination of optically pure (+)-methyl p-tolyl sulfoxide with N-chlorosuccinimide in the presence of K2CO3.The (-)-chloromethyl p-tolyl sulfoxide was alkylated to give a diastereomeric mixture of (-)-1-chloroalkyl p-tolyl sulfoxides.Addition of the anion derived from these sulfoxides to ketones or aldehydes afforded chlorohydrins in quite good yields with complete 1,2-asymmetric induction.Treatment of these chlorohydrins with a base gave optically active α,β-epoxy sulfoxides.On treatment with n-BuLi, the α,β-epoxy sulfoxides gave epoxides or allylic alcohols of high optical purity.This novel procedure was applied to a short synthesis of optically active (+)-disparlure, the sex attractant of the female gypsy moth.Aminolysis of the α,β-epoxy sulfoxides gave optically active α-amino ketones and α-amino aldehydes in quite good yields.

THE PRACTICAL PROCEDURE FOR A PREPARATION OF 1-CHLOROALKYL p-TOLYL SULFOXIDES IN HIGH OPTICALLY ACTIVE FORM: A VERY SHORT SYNTHESIS OF OPTICALLY ACTIVE DISPARLURE

A chlorination of optically active alkyl p-tolyl sulfoxides with N-chlorosuccinimide in dichloromethane in the presence of potassium carbonate afforded optically active 1-chloroalkyl p-tolyl sulfoxides in 87-94percent ee (88-94percent chemical yields).The optically active chloroalkyl sulfoxide was applied to a synthesis of optically active (+)-disparlure.

Solid-Phase Silica-Gel Catalyzed α-Halogenation of Alkyl Aryl Sulfoxides with N-Halosuccinimides

Alkyl aryl sulfoxides are readily halogenated by silica-gel supported N-halosuccinimides.The conversion of optically active alkyl 4-methylphenyl sulfoxides into 1-haloalkyl 4-methylphenyl sulfoxides is accompanied by inversion of configuration at the S-atom.The stereoselectivity of the solid-phase halogenation of alkyl aryl sulfoxides is much higher than that observrd for the halogenation in solution.