120483-06-9

Upstream product

• 201230-82-2 carbon monoxide 
• 16336-54-2 p-tolyl vinyl sulfide 
• 106-45-6 para-thiocresol 
• 107-02-8 acrolein 

Downstream Products

• 120483-22-9 (S)-1-((2R,5S,6R)-2-Benzyloxy-6-isopropyl-5-methyl-tetrahydro-pyran-2-yl)-4-hydroxy-6-p-tolylsulfanyl-hexan-2-one 
• 120483-22-9 (R)-1-((2R,5S,6R)-2-Benzyloxy-6-isopropyl-5-methyl-tetrahydro-pyran-2-yl)-4-hydroxy-6-p-tolylsulfanyl-hexan-2-one 
• 120483-07-0 (S)-4-Hydroxy-1-[(2R,5S,6R)-6-isopropyl-5-methyl-2-(2,2,2-triphenyl-ethoxy)-tetrahydro-pyran-2-yl]-6-p-tolylsulfanyl-hexan-2-one 
• 120483-08-1 (R)-4-Hydroxy-1-[(2R,5S,6R)-6-isopropyl-5-methyl-2-(2,2,2-triphenyl-ethoxy)-tetrahydro-pyran-2-yl]-6-p-tolylsulfanyl-hexan-2-one 
• 242126-90-5 4-nitro-1-p-tolylsulfanyl-pentan-3-ol 
• 1415577-52-4 C₁₃H₁₆OS 
• 1415575-81-3 C₂₆H₃₂O₂S 
• 1415577-54-6 C₁₅H₁₈O₂S 
• 1415577-53-5 C₁₇H₁₉O₄S^(1-)*Na⁽¹⁺⁾ 

Relevant academic research and scientific papers

HERBICIDE COMPOSITION

There is provided a herbicidal composition containing a cyclohexanone compound represented by Formula (I) and at least one compound selected from Group A. Group A: consisting of benoxacor, cloquintocet-mexyl, cyometrinil, dichlormid, fenchlorazole-ethyl,

CYCLOHEXANONE COMPOUNDS AND HERBICIDES COMPRISING THE SAME

The present invention provides a compound having an excellent efficacy for controlling weeds. A cyclohexanone compound of the formula (I): wherein m is an integer of 1, 2 or 3; n is an integer of any one of 1 to 5; X represents CH2, O, S, S(O)

Investigation of functionalized α-chloroalkyllithiums for a stereospecific reagent-controlled homologation approach to the analgesic alkaloid (-)-epibatidine

Four putative functionalized α-chloroakyllithiums RCH 2CHLiCl, where R=CHCH2 (18 a), CCH (18 b), CH 2OBn (18 c), and CH[O(CH2)2O] (18 d), were generated in situ by sulfoxide-lithium exchange from α-chlorosulfoxides, and investigated for the stereospecific reagent-controlled homologation (StReCH) of phenethyl and 2-chloropyrid-5-yl (17) pinacol boronic esters. Deuterium labeling experiments revealed that α-chloroalkyllithiums are quenched by proton transfer from their α-chlorosulfoxide precursors and it was established that this effect compromises the yield of StReCH reactions. Use of α-deuterated α-chlorosulfoxides was discovered to ameliorate the problem by retarding the rate of acid-base chemistry between the carbenoid and its precursor. Carbenoids 18 a and 18 b showed poor StReCH efficacy, particularly the propargyl group bearing carbenoid 18 b, the instability of which was attributed to a facile 1,2-hydride shift. By contrast, 18 d, a carbenoid that benefits from a stabilizing interaction between O and Li atoms gave good StReCH yields. Boronate 17 was chain extended by carbenoids 18 a, 18 b, and 18 d in 16, 0, and 68 % yield, respectively; α-deuterated isotopomers D-18 a and D-18 d gave yields of 33 and 79 % for the same reaction. Double StReCH of 17 was pursued to target contiguous stereodiads appropriate for the total synthesis of (-)-epibatidine (15). One-pot double StReCH of boronate 17 by two exposures to (S)-D-18 a (≤66 % ee), followed by work-up with KOOH, gave the expected stereodiad product in 16 % yield (d.r.～67:33). The comparable reaction using two exposures to (S)-D-18 d (≤90 % ee) delivered the expected bisacetal containing stereodiad (R,R)-DD-48 in 40 % yield (≥98 % ee, d.r.=85:15). Double StReCH of 17 using (S)-D-18 d (≤90 % ee) followed by (R)-D-18 d (≤90 % ee) likewise gave (R,S)-DD-48 in 49 % yield (≥97 % ee, d.r.=79:21). (R,S)-DD-48 was converted to a dideuterated isotopomer of a synthetic intermediate in Corey's synthesis of 15. Copyright

Iterative stereospecific reagent-controlled homologation using a functionalized α-chloroalkyllithium: Synthesis of cyclic targets related to epibatidine

Enantioenriched 1-chloro-2-(1,3-dioxolan-2-yl)ethyllithium was generated by PhLi initiated sulfoxide-ligand exchange and deployed in situ for sequential double stereospecific reagent-controlled homologation (StReCH) of B-(2-chloro-pyrid-5-yl) pinacol boronate. This process afforded highly functionalized contiguous stereodiad motifs (typically, % ee ≥ 98%, dr ≥ 85:15) amenable to subsequent annulative transformations as demonstrated by the concise synthesis (5-7 steps) of cyclic adducts related to the analgesic alkaloid epibatidine.

Total synthesis of (±)-phytochromobilin starting from two pyrrole derivatives

(±)-Phytochromobilin was synthesized as an acid form by developing a convenient method for the preparation of A- and D-rings starting from a 2- tosylpyrrole derivative, followed by efficient construction of A/B- and C/D- ring components via Wittig-type coupling reaction of 5-tosylpyrrolinones with 2-formylpyrrole, and palladium catalyzed deprotection of allyl esters of propanoic acid side chains at C-8 and C-12.

1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in synthesis. Highly regio- and stereoselective SN1′ and alkylation reactions

Reaction of lithiated β-sulfonyl acetals with amino acid-derived N-tosylaziridines followed by acid-catalysed cyclisation gives enantiomerically pure 2-alkyl 1,4-bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines 3 in good yields. These heterocyclic substrates react efficiently and highly stereoselectively with a range of carbon nucleophiles under Lewis acidic conditions to give the 1,2,5,6-tetrahydropyridine products of SN1′ reaction, and undergo lithiation followed by completely stereoselective reaction at the 4-position with haloalkanes.

Highly enantioselective hydroformylation of olefins catalyzed by rhodium(I) complexes of new chiral phosphine-phosphite ligands

A new chiral phosphine-phosphite ligand, (R)-2-(diphenylphosphino)- 1,1'-binaphthalen-2'-yl (S)-1,1'-binaphthalene-2,2'-diyl phosphite [(R,S)- BINAPHOS, (R,S)-2a], was synthesized. Its Rh(I) complex was prepared, and its structure has been characterized by 1H and 31P NMR spectroscopy. Using Rh(I) complexes of (R,S)-2a and its enantiomer, highly enantioselective hydroformylation of styrene has been performed (94% ee, iso/normal = 88/12). The catalyst system was also effective for a variety of other olefins. Some other phosphine-phosphite ligands bearing 1,1'-binaphthyl and biphenyl backbones, such as (S)-3,3'-dichloro-6-(diphenylphosphino)-2,2',4,4'- tetramethylbiphenyl-6'-yl (R)-1,1'-binaphthalene-2,2'-diyl phosphite [(S,R)- BIPHEMPHOS. (S,R)-5a], (R,R)-2a, (R,S)-2b, (R)-2c, and (R)-5b, were tested for asymmetric hydroformylation. The results indicate that the sense of enantioface selection for the prochiral olefins is mainly determined by the absolute configuration of the phosphine site, for example, the (R)-2- (diphenylphosphino)-1,1'-binaphthalen-2'-yl group in (R,S)-2a. The relative configurations of the two biaryl groups in the phosphine-phosphites play crucial roles in the degree of the enantioselectivities, that is, the (R,S)- isomer generally gives products in high ee's and the (R*,R*)-isomer does in low ee's. Treatment of Rh(acac)[(R,S)-2a] with a 1:1 mixture of carbon monoxide and hydrogen gave a hydridorhodium complex. RhH-(CO)2[(R,S)-2a], as a single species. Trigonal bipyramidal structure is suggested for this complex, in which the hydride and the phosphite moiety are located at the apical positions and the phosphine and the two carbonyls occupy the equatorial positions. The interchange of the phosphine and the phosphite sites with each other through rapid pseudorotations has not been observed in RhH(CO)2[(R,S)-2a]. The structural deviations of the monohydride complexes from an ideal trigonal bipyramid seem to be larger in (R*,R*)-isomers than in the corresponding (R*,S*)-isomers. The existence of only one active species involved in the Rh(1)-(R,S)-2a-catalyzed hydroformylation has been manifested by the plot of ln([R]/[S]) of the hydroformylation product vs the reciprocals of the reaction temperatures. The higher thermodynamic stability of Rh(acac)[(R,S)-2a] than its diastereomer Rh(acac)[(R,R)-2a] is demonstrated in relation to the restricted configuration of (R)-2c to (R,S)- 2c in its complex formation with Rh(1).

Asymmetric hydroformylations of sulfur-containing olefins catalyzed by BINAPHOS-Rh(I) complexes

Asymmetric hydroformylations of vinyl sulfides, allyl sulfides, and allyl sulfones catalyzed by (R,S)-BINAPHOS/Rh(acac)(CO2) afforded the corresponding branched oxo aldehydes as major products in 60-80% ee. Use of bulkier substituents on the sulfur in vinyl sulfides gave the branched oxo-aldehydes in higher regio- and enantioselectivities.