Pd-Catalyzed Asymmetric Allylic Alkylation of 3-Acetoxy-N-(tert-butyloxycarbonyl)-1,2,3,6-tetrahydropyridine – Preparation of Key Intermediates for Natural Product Synthesis

✍ Scribed by Simone Schleich; Günter Helmchen

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 322 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199910)1999:10<2515::aid-ejoc2515>3.0.co;2-g

✦ Synopsis

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