159970-79-3

Upstream product

• 93250-89-6 methyl (2R,4S)-2-(tert-butyl)-1,3-oxazolane-4-carboxylate 
• 17097-90-4 2-phenylmalonic acid monoethyl ester 
• 83-13-6 diethyl 2-phenylmalonate 
• 190080-34-3 (2RS,5S)-2-(tert-butyl)-5-methoxycarbonyl-1,3-oxazolidine 

Downstream Products

• 159970-76-0 (2R,5R)-2-tert-Butyl-6-hydroxy-8-oxo-7-phenyl-1-aza-3-oxabicyclo[3.3.0]oct-6-ene 
• 188990-91-2 (6bS,9R)-9-tert-Butyl-5-ethoxycarbonylmethyl-10-oxo-10H-8-oxa-9a-aza-pentaleno[2,1-a]naphthalene-6b-carboxylic acid methyl ester 

Relevant academic research and scientific papers

A concise approach to functionalised, homochiral tetramic acids

Dieckmann cyclisation of homochiral N-acyloxazolidines derived from serine gives good to excellent yields of α,α-disubstituted tetramic acid derivatives.

Synthetic access to 3,4-disubstituted pyroglutamates from tetramate derivatives from serine, allo-threonine and cysteine

A route allowing the conversion of substituted tetramates to 3,4-disubstituted pyroglutamates, making use of Suzuki coupling on an enol mesylate, followed by reduction, is both general and fully stereoselective.

A short synthesis of an enantiopure benzo[e]isoindolinone

An enantiopure benzo[e]isoindolinone is available by a sequence involving the reaction of a phenyl substituted tetramic acid with two equivalents of a stabilised phosphorane Ph3P = CHCO2R (R = Et or t-Bu).