Palladium-Catalyzed Asymmetric Allylic Alkylation Using Phosphine-Amide Derived from Chiral trans-2-Aminocyclohexanol

Abstract

A novel phosphine-amide derived from resolved trans-2-aminocyclohexanol has been synthesized and studied in palladium-catalyzed asymmetric allylic alkylation of racemic (E)-1,3-diphenyl-2-propenyl acetate with various nucleophiles.

Keywords:

• Asymmetric allylic alkylation
• ¹H-¹⁵N HMBC NMR
• Pd-complexes
• phosphine-amide ligand
• resolved trans-2-aminocyclohexanol

Dedicated to Professor Marian Mikołajczyk, CBMiM PAN in Łódź, Poland, on the occasion of his 70th birthday.

We thank Polonium program for support of the exchange, and K.G. thanks the MENSR for the fellowship.

Notes

^a [substrate]/[NuH]/[Base]/[Pd] = 25/75/75/1.

^b Yields of isolated pure product after column chromatography

^c Enantiomeric excess determined by HPLC analysis (column Chiralpak AD 0.46 × 25 cm).

^d The absolute configuration was determined by comparison with an authentic sample.

^e K₂CO₃ used as base.