Abstract
SN2′ reaction on the acetates obtained from vinylalumination or Baylis-Hillman products, followed by in situ reduction afforded allylic alcohols. Upon conversion to trichloroacetimidates and [3,3]-sigmatropic rearrangement, the corresponding N-protected β-substituted allylic amines were obtained in good yields. Utilization of hydroxy group as the nucleophile furnished allylic hydroxy esters, which were converted to protected α-methylene-β-amino acids via Overman rearrangement.
Original language | English (US) |
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Pages (from-to) | 2121-2124 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 46 |
Issue number | 12 |
DOIs | |
State | Published - Mar 21 2005 |
Keywords
- Allylic alcohols
- Allylic amines
- Baylis-Hillman reaction
- S2′ reaction
- Vinylalumination
- β-Amino acids