Abstract
(Chemical Equation Presented) Anti-β-substituted γ,δ- unsaturated amino acids have been synthesized via a novel design of the Eschenmoser-Claisen rearrangement. The rearrangement gives good isolated yields and excellent diastereoselectivity due to (Z)-N,O-ketene acetal formation and the pseudochairlike conformations of the reaction intermediates. Upon reductive hydrolysis, important novel amino acids and amino alcohols were synthesized for the first time via this methodology.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 4215-4218 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 8 |
| Issue number | 19 |
| DOIs | |
| State | Published - Sep 14 2006 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Qu, H., Gu, X., Min, B. J., Liu, Z., & Hruby, V. J. (2006). Synthesis of anti-β-substituted γ,δ-unsaturated amino acids via Eschenmoser-Claisen rearrangement. Organic Letters, 8(19), 4215-4218. https://doi.org/10.1021/ol061414l