124816-75-7

Upstream product

• 34233-75-5 N-ethylidenebenzylamine 
• 78605-23-9 ethyl 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane-1-acetate 
• 34233-75-5 N-ethylidenebenzylamine 
• 118975-80-7 trans-1-benzyl-3-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentyl)-4-methyl-2-azetidinone 
• 124716-47-8 1-benzyl-4-methyl-β-azetidinone 
• 124716-47-8 (S)-1-Benzyl-3-((S)-4-isopropyl-2,2-dimethyl-oxazolidin-3-yl)-4-methyl-azetidin-2-one 
• 124716-67-2 (3S,4S)-1-Benzyl-3-((S)-1-hydroxymethyl-2-methyl-propylamino)-4-methyl-azetidin-2-one 

Downstream Products

• 124816-79-1 ((2S,3S)-1-Benzyl-2-methyl-4-oxo-azetidin-3-yl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of optically active β-lactams by the photolytic reaction of imines with optically active chromium carbene complexes

Optically active chromium carbene complexes utilizing (S)-valine- and (R)-phenylglycine-derived chiral auxillaries were synthesized and subjected to photolytic reaction with a number of imines. Optically active β-lactams were produced in good to excellent chemical yield and with high diastereoisomeric excess. Procedures for removal of the chiral auxillary to produce the optically active free amino β-lactams were developed.

STEREOSELECTIVE ONE-POT SYNTHESES OF TRANS-3-AMINO-β-LACTAMS FROM ZINC ENOLATES OF N-PROTECTED α-AMINOACID ESTERS AND IMINES

A new one-pot synthesis of 3-amino-β-lactams that is based on the condensation of simple imines with zinc enolates of disilyl protected glycine esters is reported.Isolated yields are high and a trans-selectivity is observed.

Synthesis of Amino-β-lactams by the Photolytic Reaction of Imines with Pentacarbonylchromium(0)

Chromium-carbene complexes containing the group were synthesized by the reaction of Vilsmeir's salts with Cr(CO)52-.These carbenes were remarkably air stable and resistant to attack by nucleophiles.Photolytic reaction of these complexes with imines, oxazines, oxazolines, imidates, thiazines, and thiazolines produced β-lactams in fair to good yield.In most cases trans stereochemistry was observed.Representative dibenzylamino-β-lacatms were debenzylated to produce β-lactams having a free NH2 group α to the lactam carbonyl group.