476187-23-2

Upstream product

• 476187-16-3 (3R)-(8R)-(8aS)-8a-(3-[1,3]dioxolan-2-yl-propyl)-5-oxo-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-8-carboxylic acid methyl ester 
• 725250-78-2 1-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-2-(3-[1,3]dioxolan-2-yl-propyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester 
• 725250-73-7 (Z)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-6-[1,3]dioxolan-2-yl-hex-2-enoic acid methyl ester 

Downstream Products

• 486-70-4 lupinine 

Relevant academic research and scientific papers

Enantioselective synthesis of indolizidine and quinolizidine derivatives from chiral non-racemic bicyclic lactams

Chiral non-racemic bicyclic lactams 2b,c, derived from (R)- and (S)-phenylglycinol, were used in the enantioselective synthesis of (-)-lupinine and 5-epitashiromine, respectively. The efficiency of the synthesis relied on the high diastereoselectivities of formation and reduction of compounds 2b,c.

Synthesis of enantiopure cis- and trans-2,3-disubstituted piperidines

The synthesis of enantiopure cis- and trans-2,3-disubstituted piperidines 4 is described. The key step of the synthesis involves the stereoselective reduction of chiral nonracemic lactams 2 by using BH3·Me2S. A rationalization of the stereoselectivity is presented.