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The aza-

Anderson1, Flaherty, Swarbrick

  • 1School of Chemistry, University of Nottingham, Nottingham NG7 2RD, U. K.

The Journal of Organic Chemistry
|January 10, 2001
PubMed
Summary
This summary is machine-generated.

This study demonstrates a highly efficient and diastereoselective base-induced aza-[2,3]-Wittig sigmatropic rearrangement using allylic amine precursors with a C-2 trialkylsilyl group. This method enables the synthesis of valuable chemical intermediates with excellent stereochemical control.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • Allylic amines are versatile synthetic intermediates.
  • Sigmatropic rearrangements are powerful carbon-carbon bond-forming reactions.

Purpose of the Study:

  • To develop a novel base-induced aza-[2,3]-Wittig sigmatropic rearrangement.
  • To achieve high yield and diastereoselectivity in the rearrangement of allylic amine precursors.

Main Methods:

  • Introduction of a C-2 trialkylsilyl substituent into allylic amine precursors.
  • Utilizing carbonyl-based nitrogen protecting groups (e.g., N-Boc, N-benzoyl) stable to strong bases.
  • Employing migrating groups (G) that stabilize the initial anion (G-CH3 pKa > 22).

Main Results:

  • The aza-[2,3]-Wittig sigmatropic rearrangement proceeded in excellent yield.

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  • High anti diastereoselectivity (10-20:1) was achieved for products 7, 20b-d,f,g, and 23.
  • The morpholine amide derivative (Product 23) proved useful for further functionalization.

    • Conclusions:

    • The C-2 trialkylsilyl group is crucial for the efficient and diastereoselective aza-[2,3]-Wittig sigmatropic rearrangement.
    • The choice of nitrogen protecting group and migrating group significantly impacts reaction success.
    • This methodology provides a valuable route to stereochemically defined compounds.