90719-40-7

Upstream product

• 910247-04-0 (4S)-3-((Z)-7-diethylphosphoryloxy-5-methylhept-5-enoyl)-4-isopropyl-2-oxazolidinone 
• 910247-14-2 (4S)-3-((Z)-7-chloro-5-methylhept-5-enoyl)-4-isopropyl-2-oxazolidinone 
• 910247-15-3 (4S)-3-((Z)-7-bromo-5-methylhept-5-enoyl)-4-isopropyl-2-oxazolidinone 
• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 
• 4342-60-3 4-methylcyclohex-3-enecarboxylic acid 
• 90719-26-9 (4S)-3-(2-propenoyl)-4-(1-methylethyl)-2-oxazolidinone 
• 78-79-5 isoprene 
• 16695-95-7 (4'-methylcyclohex-3'-ene-1-'-yl)carbonyl chloride 
• 151153-99-0 3-[(4'-methylcyclohex-3'-ene-1'-yl)carbonyl]oxazolidin-2-one 

Downstream Products

• 121424-36-0 (+)-(1R)-4-methyl-cyclohex-3-enecarboxylic acid 
• 90719-47-4 phenylmethyl-(4R)-1-methylcyclohexene-4-carboxylate 

Relevant academic research and scientific papers

Enantioselective synthesis of α-terpineol and nephthenol by intramolecular acyloxazolidinone enolate alkylations

Enolate anions generated from norterpenyl bromides bearing oxazolidinone chiral auxiliaries at the chain termini underwent efficient, stereo-biased cyclizations to form 6- and 14-membered rings in novel synthetic routes to α-terpineol and nephthenol enantiomers. The Royal Society of Chemistry 2006.

SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one

The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions. The Royal Society of Chemistry 2006.