214072-06-7

Basic information

• Product Name: (3R,6S)-3,6-dibenzyl-3,6-dihydro-1H-pyridin-2-one
• Synonyms: (3R,6S)-3,6-dibenzyl-3,6-dihydro-1H-pyridin-2-one
• CAS NO: 214072-06-7
• Molecular Weight: 277.366
• Mol File: 214072-06-7.mol

Chemical Properties

• CAS DataBase Reference: (3R,6S)-3,6-dibenzyl-3,6-dihydro-1H-pyridin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,6S)-3,6-dibenzyl-3,6-dihydro-1H-pyridin-2-one(214072-06-7)
• EPA Substance Registry System: (3R,6S)-3,6-dibenzyl-3,6-dihydro-1H-pyridin-2-one(214072-06-7)

Safety Data

• Hazardous Substances Data: 214072-06-7(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 18598-80-6 methyl N-trityl-(S)-phenylalaninate 
• 214072-04-5 (2R,1'S)-N-(1'-benzyl-prop-2'-enyl)-N-[(2,4-dimethoxyphenyl)methyl]-2-benzyl-but-3-enamide 
• 214072-02-3 1-[N-(1'S)-(1'-benzyl-prop-2'-enyl)amino]methyl-2,4-dimethoxybenzene 
• 183509-48-0 (R)-(-)-2-benzylbut-3-enoic acid 
• 214072-03-4 (2R)-2-benzyl-3-butenoyl chloride 
• 153451-36-6 ((S)-1-Benzyl-allyl)-trityl-amine 
• 127392-99-8 N-[(2R)-2-benzyl-3-butenoyl]-(1S)-2,10-camphorsultam 
• 126410-30-8 (S)-1-phenylbut-3-en-2-amine 
• 100841-19-8 (S)-(-)-3-Phenyl-2-triphenylmethylamino-1-propanol 
• 107591-60-6 N-trityl-(S)-phenylalaninal 
• 3182-95-4 L-Phenylalaninol 
• 63-91-2 L-phenylalanine 
• 214072-05-6 (3R,6S)-N-[(2,4-Dimethoxyphenyl)methyl]-3,6-dibenzyl-3,6-dihydro-2-pyridone 

Relevant articles and documents

Diastereospecific carbonylation of π-allylpalladium complexes to give 3,6-disubstituted 3,6-dihydro-1H-pyridin-2-ones

(Ph3P)2PdCl2 was found to be the most effective of a range of catalysts for decarboxylative carbonylation of (4S,5RS)-5-ethenyl-4-(2-propyl)oxazolidin-2-one to give the δ-lactam, (6S)-3,6-dihydro-6-(2-propyl)-1H-pyridin-2-one. In a similar way, diastereoisomerically pure (4S,5S)-4-benzyl-5-((Z)alk-1-enyl)oxazolidin-2-ones undergo stereospecific carbonylation to give (3R,6S)-6-benzyl-3-alkyl-3,6-dihydro-1H-pyridin-2-ones. The diastereoisomeric (4S,5R)-4-benzyl-5-((Z)alk-1-enyl)oxazolidin-2-ones give rise to a separable mixture of the corresponding (3S,6S)-6-benzyl-3-alkyl-3,6-dihydro-1H-pyridin-2-one and (4S,5S)-4-benzyl-5-((E)alk-1-enyl)oxazolidin-2-one. Under more forcing conditions, the latter oxazolidinone is carbonylated to the 3,6-anti-pyridinone. The stereochemical course of the reactions can be rationalized by formation of a π-allyl palladium cation with inversion of configuration followed by carbonylation with retention. The stereospecificity observed in our system precludes metal-metal exchange of the π-allyl complexes by a Pd(0) displacement process.

An access to (Z)-ethylenic pseudodipeptides based on ring-closing metathesis

A new access to enantiopure (Z)-ethylenic pseudopeptides, starting from the chiral pool of amino acids and enantiopure 2-substituted-but-3-enoic acids is proposed and illustrated by the syntheses of the (Z)-ethylenic pseudopeptidic analogs of L-Phe-L-Phe, L-Phe-D-Phe, L-Phe-L-Val, L-Phe-D-Val and racemic (LL,DD) and (LD,DL) (phenyl)Gly-Phe. The key-steps of these syntheses are a ring-closing metathesis, catalysed by Grubbs' ruthenium alkykidene complexes, on diethylenic amides and the hydrolytic cleavage of the resulting dihydropyridones under mild conditions through intermediate formation of cyclic imidates.

Enantioconservative synthesis and ring closing metathesis of disubstituted dialkenic amides

Optically pure disubstituted dialkenic amides 2, which are direct precursors of Z-ethylenic pseudo-peptides 1, are readily synthesized and then cyclized to lactams 3 in the presence of Grubbs' ruthenium-based metathesis catalysts with total conservation of enantiomeric purity.