Stereoselective Synthesis of cis-and trans-Beta,Gamma-Unsaturated Carboxylic Esters via Reaction of Alkenyldichloroboranes with Ethyl Diazoacetate

Abstract

Trans-Alkenyldichloroboranes, easily prepared by the reaction of dichloroborane-dimethyl sulfide complex with various alkynes in the presence of boron trichloride, react smoothly with ethyl diazoacetate at -65 C with the liberation of nitrogen. Treatment of the intermediates with methanol-water produces trans-Beta, gamma-unsaturated carboxylic esters stereoselectively in good yields. Similar treatment of cis-alkenyldichloroboranes provides the corresponding cis-Beta, gamma unsaturated esters.

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Document Details

Document Type
Technical Report
Publication Date
Jul 16, 1991
Accession Number
ADA239049

Entities

People

  • Ashok M. Salunkhe
  • Herbert C. Brown

Organizations

  • Purdue University

Tags

DTIC Thesaurus Topics

  • Abstracts
  • Alcohols
  • Chemical Synthesis
  • Chemistry
  • Contracts
  • Diazo Compounds
  • Ethers
  • Governments
  • Mass Spectra
  • Methanols
  • Military Research
  • National Governments
  • Nitrogen
  • Procurement
  • United States
  • United States Government
  • Universities

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry