(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)|
|Number of pages||4|
|State||Published - Sep 14 2006|
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
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CCDC 620695: Experimental Crystal Structure Determination
Qu, H. (Creator), Carducci, M. D. (Creator), Nichol, G. S. (Creator) & Hruby, V. J. (Creator), Cambridge Crystallographic Data Centre, 2006
DOI: 10.5517/ccntwfr, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccntwfr&sid=DataCite