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Pd-Catalyzed Asymmetric Allylic Alkylation of 3-Acetoxy-N-(tert-butyloxycarbonyl)-1,2,3,6-tetrahydropyridine - Preparation of Key Intermediates for Natural Product Synthesis (1999)

Schleich, Simone ; Helmchen, Günter

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 2515-2521

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Details

ISSN: 1434-193X

Keywords: Asymmetric synthesis ; Heterocycles ; Palladium ; Alkylations ; Allyl complexes ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

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