251948-97-7

Upstream product

• 501-53-1 benzyl chloroformate 
• 251948-89-7 acetic acid 1-[(allyl-tert-butoxycarbonyl-amino)-methyl]-allyl ester 
• 224779-26-4 N-allyl-N-(2-hydroxy-but-3-enyl)-carbamic acid tert-butyl ester 
• 251948-90-0 3-acetoxy-N-(tert-butyloxycarbonyl)-1,2,3,6-tetrahydropyridine 
• 251948-91-1 (-)-(S)-2-(N-tert-butyloxycarbonyl-1,2,3,6-tetrahydropyridin-3-yl)-malonic acid dimethyl ester 

Downstream Products

• 251948-98-8 (-)-(R)-2-(N-benzyloxycarbonyl-1,2,3,6-tetrahydropyridin-3-yl)-acetic acid methyl ester 

Relevant academic research and scientific papers

Pd-catalyzed asymmetric allylic alkylation of 3-acetoxy-N-(tert- butyloxycarbonyl)-1,2,3,6-tetrahydropyridine - Preparation of key intermediates for natural product synthesis

A convenient synthesis of racemic tetrahydropyridine 1 was developed. Pd-catalyzed allylic alkylation of 1 with malonate and dimethylacetoxymalonate as nucleophiles with the phosphanylcarboxylic acid L1 and the dihydrooxazol L2 as ligands, were carried out and gave enantiomeric excesses of up to 98%. Absolute configurations were determined for all compounds described. From the alkylation products (+)- and (-)-2a, and (+)- and (-)-2b a variety of versatile, nonracemic chiral intermediates were prepared.