Highly diastereoselective synthesis of beta-carboxy-gamma-lactams and their ethyl esters via Sc(OTf)(3)-catalyzed imino Mukaiyama-aldol type reaction of 2,5-bis(trimethylsilyloxy)furan with imines

J Org Chem. 2007 Jun 22;72(13):5016-9. doi: 10.1021/jo070533r. Epub 2007 May 17.

Abstract

Functionalized gamma-lactams are found to be crucial intermediates in the synthesis of biologically important natural products. We herein described a highly diastereoselective synthesis of beta-carboxy-gamma-lactams and their ethyl ester derivatives, in high yields with high diastereomeric ratio, via the Mukaiyama-aldol type reaction of 2,5-bis(trimethysilyloxy)furan with imines, employing Sc(OTf)(3) as a catalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemistry*
  • Catalysis
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Ethylenes / chemistry*
  • Furans / chemistry*
  • Imines / chemistry*
  • Lactams / chemical synthesis*
  • Lactams / chemistry
  • Mesylates / chemistry*
  • Molecular Structure
  • Scandium / chemistry*
  • Stereoisomerism
  • Trimethylsilyl Compounds / chemistry*

Substances

  • 2,5-bis(trimethylsilyloxy)furan
  • Carboxylic Acids
  • Esters
  • Ethylenes
  • Furans
  • Imines
  • Lactams
  • Mesylates
  • Trimethylsilyl Compounds
  • scandium triflate
  • ethylene
  • Scandium