Allenyl-β-lactams: versatile scaffolds for the synthesis of heterocycles

Chem Rec. 2011 Dec;11(6):311-30. doi: 10.1002/tcr.201100011. Epub 2011 Nov 4.

Abstract

The hybrid allenic β-lactam moiety represents an excellent building block for carbo- and heterocyclization reactions, affording a large number of cyclic structures containing different sized skeletons in a single step. This strategy has been studied under thermal and radical-induced conditions. More recently, the use of transition-metal catalysis has been introduced as an alternative that relies on the activation of the allenic component. On the other hand, the intramolecular version has attracted much attention as a strategy for the synthesis of bi- and tricyclic compounds in a regio- and stereoselective manner. This overview focuses on the most recently developed cyclizations on 2-azetidinone-tethered allenes along with remarkable early works accounting for the mechanism, as well as for the regio- and diastereoselectivities of the cyclizations.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Alkynes / chemistry
  • Catalysis
  • Cyclization
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry*
  • Metals / chemistry
  • Selenium / chemistry
  • Stereoisomerism
  • beta-Lactams / chemical synthesis
  • beta-Lactams / chemistry*

Substances

  • Alkynes
  • Heterocyclic Compounds
  • Metals
  • beta-Lactams
  • Selenium