21963-41-7Relevant articles and documents
Enantioselective Synthesis of ((1 R,2 R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate
Ravi Ganesh,Pachore, Sharad S.,Pratap,Umesh,Basaveswara Rao,Murthy,Suresh Babu
supporting information, p. 2676 - 2682 (2015/12/18)
A concise, economical, and highly enantioselective synthesis of bismesylate intermediate of lurasidone HCl, an antipsychotic, has been developed. The key steps involved in the synthesis are thionyl chloride-catalyzed esterification of tetrahydrophthalic anhydride in MeOH, epimerization of cis to trans isomer, hydrolysis of the diester, resolution of the diacid, reduction with Red-Al, and finally bismesylation of the corresponding diol, which provided the desired intermediate ((1 R,2 R)-cyclohexane-1,2-diyl)bis(methylene) dimethanesulfonate in overall good yield.
Rational tuning chelate size of bis-oxazoline ligands to improve enantioselectivity in the asymmetric aziridination of chalcones
Ma, Linge,Du, Da-Ming,Xu, Jiaxi
, p. 10155 - 10158 (2007/10/03)
Chalcones were asymmetrically aziridinated with [N-(p-toluenesulfonyl) imino]phenyliodinane (PhI=NTs) as a nitrene source under catalysis of CuOTf and a series of cyclohexane-linked bis-oxazolines (cHBOXes), which are chelate size rationally tuned bis-oxazolines. The results indicate that highly enantioselective aziridination of chalcones with up to >99% ee have been achieved under catalysis of (S,S)-1,2-bis[(S)-(4-phenyl)oxazolin-2-yl] cyclohexane, which is the most-matched stereoisomer among cyclohexane-linked bis-oxazolines. It was also found that the enantioselectivity is not substituent-dependent with respect to chalcones in the present case, unlike with 1,8-anthracene-linked bis-oxazolines (AnBOXes).
Synthesis of new C2-symmetrical diphosphines using chiral zinc organometallics
Longeau, Alexia,Durand, Sandrine,Spiegel, Anja,Knoechel, Paul
, p. 987 - 990 (2007/10/03)
The new C2-symmetrical diphosphines 1-4 of potential interest for asymmetric catalysis were prepared in protected form by a convergent synthesis based on the use of readily available (S,S)-1,2-cyclohexanedicarboxylic acid 8 and the phosphorus reagent (Et2N)2PLi·BH3.