321885-29-4

Upstream product

• 177944-16-0 (R)-N-(but-3-en-1-yl)-N-(α-methylbenzyl)amine 
• 1345893-78-8 tert-butyl but-3-enyl(R)-1-phenylethylcarbamate 
• 1345893-81-3 (R)-tert-butyl 5-oxoctyl(1-phenylethyl)carbamate 
• 321885-25-0 N-(1-phenyl-ethyl)-N-(1-propyl-vinyl)-acrylamide 
• 321885-23-8 [1-Methyl-but-(Z)-ylidene]-((R)-1-phenyl-ethyl)-amine 
• 107-87-9 2-Pentanone 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 321885-27-2 N-(α-methylbenzyl)-6-propylpiperidin-2-one 

Downstream Products

• 458-88-8 coniine 

Relevant academic research and scientific papers

Diastereoselective access to nonracemic 2-cis-substituted and 2,6-cis-disubstituted piperidines

Access to nonracemic amino ketones via a hydrozirconation/transmetalation/ acylation sequence applied to Boc-protected 1-aminobut-3-enes is presented. This method was applied to the stereoselective synthesis of cyclic imines (or iminiums) which were diastereoselectively converted into 2-cis-substituted and 2,6-cis-disubstituted piperidines. The potential of this approach in the field of alkaloid synthesis was illustrated by the synthesis of (-)-coniine and (-)-indolizidine 209D. Furthermore, access to indolizidines bearing a quaternary center could also be envisioned through this strategy.

A new asymmetric synthesis of (S)-(+)-pipecoline and (S)-(+)- and (R)-(-)-coniine by reductive photocyclization of dienamides

(S)-(+)-Pipecoline and both enantiomers of coniine were synthesized, in good yields, by a reductive photocyclization of chiral dienamides. Enantioselectivities of up to 75% were obtained. (C) 2000 Published by Elsevier Science Ltd.