197142-90-8

Upstream product

• 151302-17-9 (S)-2-(N,N-dibenzylamino)-2-phenylacetic acid (R)-pantolactone ester 
• 100-52-7 benzaldehyde 
• 135357-90-3 (2R)-N-benzyl-2-amino-2-phenyl-1-ethanol 
• 1417715-01-5 O,O'-di(α-dibenzylamino-α-phenylacetyl)-N,N,N',N'-tetramethyl-L-tartaric diamide 
• 20989-17-7 (2S)-2-phenylglycinol 
• 100-44-7 benzyl chloride 
• 205748-19-2 (R,S)-2-Bromo-2-phenylacetic acid (R)-pantolactone ester 
• 4870-65-9 2-bromophenylacetic acid 
• 2935-35-5 (S)-2-phenylglycine 
• 192439-50-2 (S)-Dibenzylamino-phenyl-acetic acid benzyl ester 
• 100-39-0 benzyl bromide 

Downstream Products

• 89160-45-2 (4R)-(+)-4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 421551-20-4 ((1S,2S)-2-Dibenzylamino-1-hydroxy-2-phenyl-ethyl)-phosphonic acid diethyl ester 
• 421551-18-0 ((1S,2S)-2-Dibenzylamino-1-hydroxy-2-phenyl-ethyl)-phosphonic acid dimethyl ester 
• 294842-98-1 dimethyl (1S,2S)-2-[(tert-butoxycarbonyl)amino]-1-hydroxy-2-phenylethylphosphonate 

Relevant academic research and scientific papers

Chiral N-heterocyclic carbene-iridium complexes for asymmetric reduction of prochiral ketimines

Enantioselective reduction of imines to the corresponding chiral secondary amines has been studied using a series of chiral half-sandwich iridium complexes. Chiral N-heterocyclic carbene (NHC) ligands in these complexes were synthesized from readily available, naturally occurring amino acids. Inexpensive phenylsilane was used as a convenient hydrogen donor. Under the optimized conditions, Ir-NHC complexes could reduce ketimines in good yields, albeit with moderate enantiomeric excess (ee). The phenylglycine derived chiral NHC was shown to give the best Ir catalyst and it also gave the maximum ee compared to catalysts prepared from other NHCs in this series. The opposite enantiomer of the reduction product was always obtained while using the Ir complex bearing a valine based NHC. The yields were consistently high with a variety of imine substrates having different steric and electronic demands.

BENZOLACTAM COMPOUNDS AS PROTEIN KINASE INHIBITORS

The invention provides a compound of formula (0): or a pharmaceutically acceptable salt, N-oxide or tautomer thereof. The compounds are inhibitors of ERK 1/2 kinases and will be useful in the treatment of ERKl/2-mediated conditions. The compounds are therefore useful in therapy, in particular in the treatment of cancer.

Stereoselective and regioselective intramolecular Friedel-Crafts reaction of aziridinium ions for synthesis of 4-substituted tetrahydroisoquinolines

Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel-Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziri

Stereoselective formation and rearrangement of morpholinium ylides derived from copper carbenoids

Amino diazoacetoacetates 4a-e and 7a,b were prepared from readily available amino alcohols and subjected to copper-catalyzed carbene-transfer reaction. Substrates 4c-e furnished the morpholin-2-ones 5c-e in good yield via the corresponding cyclic ammonium ylides, albeit with poor diastereoselectivity. Substrates 4a,b failed to provide the corresponding morpholinones, perhaps as a result of steric congestion. Cyclic substrates 7a,b underwent conversion to bicyclic morpholinones 8 and 9 in good yield and with moderate to good diastereoselectivity. This result is rationalized via control of the transiently stereogenic ammonium center of the intermediate bicyclic ylides.

Stereoselective deprotonation of chiral and achiral 2-aminoalkyl carbamates: Synthesis of optically active β-amino alcohols via 1-oxy- substituted alkyllithium intermediates

A facile protocol for the electrophilic C-substitution (methylation, acylation, α-hydroxyalkylation, and carboxylation) of several 2-(N,N- dibenzylamino)alkan-1-ols via the carbamates 10 is reported. The stereochemistry of the lithiation is greatly influenced by the complexing diamine. The substrate-directed selection between the diastereotopic a-pro-R and pro-S protons in the TMEDA-assisted deprotonation is largely shifted towards pro-S-selectivity in the presence of (-)-sparteine (4). Each of both diastereomeric series is readily accessible in several cases.

Synthesis of enantiopure syn-β-amino alcohols. A simple case of chelation-controlled additions of diethylzinc to α-(dibenzylamino) aldehydes

Enantiomerically pure syn-2-amino alcohols 6 are prepared by addition of diethylzinc to chiral α-(dibenzylamino) aldehydes 4. The addition is highly stereoselective, leading to syn-2-(dibenzylamino) alcohols 5 with excellent diastereomeric excesses (76-98%). Debenzylation of 5 by hydrogenolysis on Pearlman's catalyst yields quantitatively the amino alcohols 6.