174618-40-7

Upstream product

• 95497-24-8 4-butyl-1,5-dihydropyrrol-2-one 
• 264903-64-2 [2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-(4-methoxy-phenyl)-amine 
• 264903-87-9 Methanesulfonic acid (S)-2-hydroxy-2-[1-(4-methoxy-phenyl)-5-oxo-pyrrolidin-3-yl]-ethyl ester 
• 264903-66-4 N-[{(S)-3,4-dihydroxy-3,4-O-isopropylidene}butyl]-N-(4-methoxyphenyl)-α-carbomethoxy-α-diazoacetamide 
• 264903-65-3 N-[{(S)-3,4-dihydroxy-3,4-O-isopropylidene}butyl]-N-(4-methoxyphenyl)-α-(carbomethoxy)acetamide 
• 247943-18-6 4-[{(S)-1,2-dihydroxy-1,2-O-isopropylidene}ethyl]-3-carbomethoxy-1-(4-methoxyphenyl)-2-pyrrolidinone 
• 264903-89-1 4-[(1S)-1-hydroxybutyl]-1-(4-methoxyphenyl)-2-pyrrolidinone 
• 264903-79-9 4-[{(S)-1,2-dihydroxy-1,2-O-isopropylidene}ethyl]-1-(4-methoxyphenyl)-2-pyrrolidinone 
• 264903-80-2 4-((S)-1,2-Dihydroxy-ethyl)-1-(4-methoxy-phenyl)-pyrrolidin-2-one 
• 264903-63-1 (S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide 
• 264903-88-0 1-(4-Methoxy-phenyl)-4-(S)-oxiranyl-pyrrolidin-2-one 

Relevant academic research and scientific papers

Catalytic enantioselective conjugate reduction of lactones and lactams

A dramatic acceleration of the enantioselective copper-catalyzed conjugate reduction of α,β-unsaturated lactones, lactams, and esters is reported upon addition of alcohol additives. Good to excellent yields and enantioselectivities were realized using a catalyst generated in situ from CuCl2·H2O, t-BuONa, p-tol-BINAP, and PMHS, and this methodology was applied to the synthesis of (-)-Paroxetine.

Studies on the Rh(II)-catalyzed C-H insertion reaction of some derivatives of N-[4-{(S)-1,2-dihydroxybutyl}]-α-diazoanilides: Site- selectivity

The Rh(II)-catalyzed reactions of diazoamides (1a, c-e) were investigated. The results show that both steric and electronic effects work in concert to govern the regio- and chemo-selectivity of the reaction. The diastereoselectivity of the reaction in the

Steric and Electronic Influences on the Diastereoselectivity of the Rh2(OAc)4-Catalyzed C-H Insertion in Chiral Ester Diazoanilides: Synthesis of Chiral, Nonracemic 4-Substituted 2-Pyrrolidinones

A series of N-substituted N-(4-methoxyphenyl)-α-(alkoxycarbonyl)-α-diazoacetanilides, 10 and ent-10, wherein the alkoxy unit is a chiral auxiliary group [(-)-7 or (+)-8)], was prepared. The Rh2(OAc)4-catalyzed intramolecular C-H insertion reaction of 10 and ent-10, under optimized reaction conditions, was investigated as a route for the preparation of chiral, nonracemic 4-substituted 2-pyrrolidinones. The cyclization reaction led only to 2-pyrrolidinone and 2-azetidinone products; the former products were obtained as major and, in a few cases, as exclusive products. The type and nature of the N-substituent in 10 or ent-10 was found to govern the diastereoselectivity of the reaction. With N-alkyl groups, steric effects play an important role in determining the diastereoselectivity of the reaction. However, with N-arylethyl substituents, electronic effects transmitted by the aryl substituents influenced the diastereoselectivity of the C-H insertion reaction. Specifically, electron-donating substituents were found to markedly attenuate the diastereoselectivity of the reaction. The diastereoselectivity of the reaction ranged from moderate to high (37-98%). A transition-state model to explain the observed diastereoselectivity is provided. The synthetic utility of the method is demonstrated by the stereoselective synthesis of the medicinally important, unnatural amino acid trans-4-cyclohexyl-L-proline 23.