American Chemical Society
ja069312d_si_003.pdf (276.08 kB)

Enantioselective Conjugate Addition of Hydrazines to α,β-Unsaturated Imides. Synthesis of Chiral Pyrazolidinones

Download (276.08 kB)
journal contribution
posted on 2007-04-18, 00:00 authored by Mukund P. Sibi, Takahiro Soeta
This manuscript describes a highly enantioselective conjugate hydrazine addition to α,β-unsaturated imides. The achiral template used has a significant impact on product enantioselectivity. Reactions at lower temperatures provide a protocol to add substituted hydrazines with selectivity resulting in the formation of a single pyrazolidinone product (>98:2 selectivity). A variety of chiral pyrazolidinones with potential as chiral auxiliaries and ligands are accessible through the new conjugate addition methodology.