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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
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Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
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Allene ether Nazarov cyclization.

Marcus A Tius1

  • 1University of Hawaii, 2545 The Mall, Honolulu, Hawaii 96822, USA. tius@hawaii.edu.

Chemical Society Reviews
|November 8, 2013
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Summary
This summary is machine-generated.

Alkoxyallenes are versatile reagents enabling diverse applications, particularly in Nazarov cyclization reactions. This report details their use in various oxidative, enantioselective, and diastereoselective Nazarov cyclizations, including applications in natural product synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Asymmetric Synthesis

Background:

  • Alkoxyallenes exhibit high reactivity and ease of synthesis.
  • The Nazarov cyclization is a powerful tool for carbocycle formation.

Purpose of the Study:

  • To review the applications of alkoxyallenes in Nazarov cyclization reactions.
  • To highlight advancements in enantioselective and diastereoselective versions.
  • To showcase utility in total synthesis.

Main Methods:

  • Oxidative cyclization of vinyl alkoxyallenes.
  • Nazarov cyclizations involving ketones and carbinols.
  • In situ generation of alkoxyallenes from propargyl ethers on solid supports.

Main Results:

  • Development of chiral auxiliaries for highly enantioselective Nazarov cyclizations.
  • Establishment of diastereoselective, chiral auxiliary-controlled reactions.
  • Demonstration of methodology in natural product synthesis.

Conclusions:

  • Alkoxyallenes are key components in versatile Nazarov cyclization strategies.
  • Significant progress has been made in controlling stereoselectivity.
  • The methodology is valuable for complex molecule synthesis.