Asymmetric Co(II)-catalyzed cyclopropanation with succinimidyl diazoacetate: general synthesis of chiral cyclopropyl carboxamides

Joshua V Ruppel; Ted J Gauthier; Nicole L Snyder; Jason A Perman; X Peter Zhang

doi:10.1021/ol9005882

Asymmetric Co(II)-catalyzed cyclopropanation with succinimidyl diazoacetate: general synthesis of chiral cyclopropyl carboxamides

Org Lett. 2009 Jun 4;11(11):2273-6. doi: 10.1021/ol9005882.

Authors

Joshua V Ruppel¹, Ted J Gauthier, Nicole L Snyder, Jason A Perman, X Peter Zhang

Affiliation

¹ Department of Chemistry, University of South Florida, Tampa, Florida 33620-5250, USA.

PMID: 19413344
DOI: 10.1021/ol9005882

Abstract

[Co(P1)] is an effective catalyst for asymmetric cyclopropanation with succinimidyl diazoacetate. The Co(II)-catalyzed reaction is suitable for various olefins, providing the desired cyclopropane succinimidyl esters in high yields and excellent diastereo- and enantioselectivity. The resulting enantioenriched cyclopropane succinimidyl esters can serve as convenient synthons for the general synthesis of optically active cyclopropyl carboxamides.