221128-71-8

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 100-39-0 benzyl bromide 
• 221128-55-8 Pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester 
• 5427-82-7 1H-pyrrole-2-carbonyl chloride 
• 221128-67-2 Pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-[(1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester 
• 634-97-9 pyrrole-2-carboxyl acid 
• 221128-69-4 (S)-2-Benzyl-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-[(1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester 

Relevant academic research and scientific papers

The stereoselective Birch reduction of pyrroles

The Birch reduction has been applied to electron-deficient pyrroles substituted with a chiral auxiliary at the C-2 position. Using either 8- phenylmenthol or trans-2-(α-cumyl)cyclohexanol (TCC) as auxiliaries, high levels of stereoselectivity were obtained. Moreover, the auxiliary could be removed using a high-yielding three-step sequence to furnish substituted dehydroproline derivatives with high enantiomeric purity. By choosing either (-)-8-phenylmenthol or (+)-TCC as an auxiliary either enantiomer of the dehydroproline product could be obtained.