6090-01-3

Upstream product

• 18826-95-4 1.3-butanediol 
• 108-88-3 toluene 
• 39027-57-1 3-(4-methylphenyl)butanoic acid 
• 6090-00-2 (+/-)-ethyl 3-(4-methylphenyl)butanoate 
• 100058-36-4 3-(p-tolyl)tetrahydrofuran 
• 122-00-9 para-methylacetophenone 
• 94853-53-9 ethyl 3-(4-methylphenyl)-2-butenoate 
• 29128-22-1 3-(4-methylphenyl)-3-buten-1-ol 
• 14271-34-2 β-methyl 4-methylphenylacrylic acid 
• 6305-61-9 ethyl (E)-3-p-tolylbut-2-enoate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 2167-39-7 (+/-)-2-methyloxetane 

Downstream Products

• 5838-08-4 1-(3-bromo-1-methyl-propyl)-4-methyl-benzene 
• 43208-94-2 1-Iod-3-p-tolylbutan 
• 38142-58-4 (+/-)-ar-turmerone 
• 88065-35-4 2-methyl-6-(p-tolyl)-3-phenylthioheptan-4-one 
• 88065-34-3 2-methyl-6-(p-tolyl)-3,3-bisphenylthioheptan-4-ol 
• 98711-79-6 2-methyl-6-(p-tolyl)-3-phenylsulphinylheptan-4-one 
• 6089-98-1 10-(p-Tolyl)-2-methyl-6-methylen-undecen-⁽²⁾ 
• 26127-21-9 2-Methyl-6-oxo-10-p-tolyl-undeca-2-en 
• 6090-03-5 2-Methyl-6-oxo-10-(p-tolyl)-undec-2-en-7-carbonsaeure-ethylester 
• 39599-18-3 6-(p-tolyl)-2-methyl-2-heptanol, trans- 

Relevant academic research and scientific papers

Helical triskelion monophosphites as ligands in asymmetric catalysis

Members of a new family of chiral triskelion P ligands, namely helical C3-symmetric monophos- phites P(OR)3, have been prepared in two steps Dy monoacylation of (R)- or (S)-1,1'-binaphthyl-2,2'-diol (BINOL) or diphenol using a carboxylic acid chloride followed Dy PCl3 phosphorylation. The most sterically hindered member of these monophosphites, derived from the compound accessible by monoacylation of BINOL using adamantane carboxylic acid chloride, has been characterized by X-ray crystallography and NMR spectroscopy as a single well-defined compound. It exists exclusively in the syn conformation, with a propeller-like (twisted) geometry resulting in helicity. Upon utilization of(R)- or (S)-BINOL in the two-step synthesis, the helicity proves to be P or M, respectively. When used as ligands in the Rh-catalyzed asymmetri c hydrogenation of prochiral homoallylic alcohols, these bulky helical ligands lead to respectable enantioselectivities (79-98percent ee). In contrast, the less sterically congested and more flexible BINOL-derived phenyl analogue exists in several conformeric forms, even in the crystal, and this leads to poor enantioselectivity in the model reactions (ee = 32percent). For the purpose of structural comparison, the analogous monophosphites derived from diphenol were also prepared and characterized. These compounds, again in contrast to the BINOL-derived adamantyl derivatives, occur in several different conformeric states.

Stereoselective radical Aryl migration reactions from sulfur to carbon

Stereoselective aryl migration reactions from sulfur in sulfonates and sulfonamides to C-centered radicals are reported. The 1,5-aryl migration from sulfur to differently substituted C-centered radicals could be performed with high yields and selectivities. Functionalized aryl groups could also be transferred by this new method. A model to explain the stereochemical outcome of the reaction is presented and some mechanistic aspects of this reaction are discussed. Aryl migration reactions from sulfur in sulfinates to carbon radicals were less efficient, and the corresponding migrations in aryl sulfoxides were not observed at all. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Baker's yeast mediated enantioselective synthesis of the bisabolane sesquiterpenes curcumene, turmerone, dehydrocurcumene and nuciferal

Fermenting baker's yeast converts the allylic alcohol 6 into enantiomerically pure (S)-(+)-3-(p-tolyl)butan-1-ol 7 which is a useful chiral building block for the synthesis of bisabolane sesquiterpenes. The versatility of this approach is shown in the preparation of (S)-(+)-curcumene, (S)-(+)-turmerone, (S)-(+)-dehydrocurcumene and (E,S)-(+)-nuciferal.

Generality and Mechanism of Homobenzylic-Homoallylic Hydrogenolysis of 5-Aryl-4,5-dihydro-1,3-dioxepins

Birch reduction of several 5-aryl-4,5-dihydro-1,3-dioxepins gave rise to 3-arylbutanal in moderate to good yields by hydrogenolytic cleavage of the homobenzylic-homoallylic carbon-oxygen bond when the benzylic-allylic carbon is tertiary.However, the reaction did not take place when the benzylic-allylic carbon is quaternary.Moreover, the reaction was found to proceed with complete racemization at the benylic-allylic center indicating a concurrent elimination-reduction pathway to be involved.

A Regiospecific Route to Conjugated Enones via α-Phenylthio Ketones

2,5-Dimethylhex-4-en-3-one, E-6-methylhept-2-en-4-one, E-7-methyloct-4-en-3-one, ar-tumerone, and E-7-oxo-oct-5-enoic acid were synthesized regiospecifically via α-phenylthio ketones from bisphenylthio carbanions and aldehydes.

REGIOSPECIFIC SYNTHESIS OF ENONES VIA α-(PHENYLTHIO)-KETONES: 2,5-DIMETHYL-4-HEXEN-3-ONE, E-6-METHYL-2-HEPTEN-4-ONE, E-7-METHYL-4-OCTEN-3-ONE, AND AR-TURMERONE

Enones not available from aldol condensations may be synthesised regiospecifically via α-(phenylthio)ketones: the title compounds have been made by this route.