24176-68-9Relevant academic research and scientific papers
Enantioselective inclusion of (R)-phenylglycyl-(R)-phenylglycine with benzyl methyl sulfoxides
Akazome, Motohiro,Hirabayashi, Atsushi,Ogura, Katsuyuki
, p. 12085 - 12093 (2004)
A crystalline dipeptide, (R)-phenylglycyl-(R)-phenylglycine (RR-1), recognized p-halobenzyl methyl sulfoxides with high R-enantioselectivity (86-99% ee) to form inclusion compounds. The single-crystal X-ray analyses showed that RR-1 molecules are arranged in parallel and zigzags via hydrogen bonding to construct a pleated sheet. The guest molecules that form hydrogen bond with +NH3 of RR-1 are accommodated in the channel cavity between the layers. In contrast to the inclusion crystals of parent benzyl methyl sulfoxide, in which a rectangular cavity is formed, the cavity including p-halobenzyl methyl sulfoxides becomes rhomboidal. We also examine the guest exchange in these inclusion compounds and it was found that the guest exchanges occur when the host structure changes. Graphical Abstract.
Methanesulfinylation of Benzyl Halides with Dimethyl Sulfoxide
Fu, Duo,Dong, Jun,Du, Hongguang,Xu, Jiaxi
, p. 2752 - 2758 (2020/01/31)
A phenyltrimethylammonium tribromide-mediated nucleophilic substitution/oxygen transformation reaction of benzyl halides with DMSO has been developed. In this transition-metal-free reaction, DMSO acts as not only a solvent but also a "S(O)Me" source, thus providing a convenient method for the efficient and direct synthesis of various benzyl methyl sulfoxides.
BIOTRANSFORMATION OF ORGANIC SULFIDES. PART 6. FORMATION OF CHIRAL para-SUBSTITUTED BENZYL METHYL SULFOXIDES BY HELMINTHOSPORIUM SPECIES NRRL 4671
Holland, Herbert L.,Brown, Frances M.,Larsen, Brett G.
, p. 1561 - 1568 (2007/10/02)
The fungus Helminthosporium species NRRL 4671 has been used for the biotransformation of a series of para-substituted benzyl sulfides with substituent groups consisting of trifluoromethyl, halo, hydroxy, methoxy, acetoxy, nitro, cyano, amino, acetamido, acyl and carboxylic acid units.In all cases, sulfoxide formation occurred in good yoeld and with predominant (S) chirality at the sulfur position.A minor amount of sulfone product was also obtained from the halo- and methoxy-substituted substrates.
