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Related Experiment Videos

Cyclopropane structural units from homoaldol adducts.

Richard E Taylor1, Christina A Risatti, F Conrad Engelhardt

  • 1Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA. taylor.61@nd.edu

Organic Letters
|April 12, 2003
PubMed
Summary

A new two-step method efficiently converts aldehydes into cyclopropylaldehydes using enecarbamates. This process yields cyclopropylaldehydes with high selectivity and allows for the isolation of related carbinol and amine products.

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Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J.

Chemistry (Weinheim an der Bergstrasse, Germany)·2021

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Aldehyde homologation is crucial for synthesizing complex organic molecules.
  • Developing selective and efficient methods for creating cyclopropyl structures remains an active area of research.

Purpose of the Study:

  • To develop an efficient two-step method for the homologation of aldehydes to cyclopropylaldehydes.
  • To investigate the stereoselectivity of the cyclopropanation reaction.
  • To explore the trapping of reaction intermediates for the synthesis of related compounds.

Main Methods:

  • Activation of homoaldol adducts derived from O-enecarbamates and N-enecarbamates.
  • Utilizing specific reaction conditions to promote cyclopropanation.
  • Trapping of oxonium and iminium ion intermediates.

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Main Results:

  • High yields of cyclopropylaldehydes were achieved.
  • Good to excellent levels of trans/cis selectivity were observed in the cyclopropanation.
  • Successful trapping of intermediates led to the direct isolation of cyclopropyl carbinol and cyclopropylamine products.

Conclusions:

  • The developed two-step method provides an efficient route to cyclopropylaldehydes.
  • The reaction offers good stereochemical control.
  • The methodology allows for diversification into cyclopropyl carbinol and cyclopropylamine derivatives.