Si-free enolate Claisen rearrangements of enamido substrates.
α-Alkyl β-amino esters are available in high diastereoselectivity through a silicon-free Claisen enolate [3,3]-sigmatropic rearrangement of enamide esters. Optimisation studies have probed the crucial role of the initial enolisation and the nature of the enamide N-centre. The demonstration of chirality transfer and the formation of β-proline systems, is also presented.
Department of Chemistry, University of Bath, Bath, United Kingdom BA2 7AY.
Wesley R R
WR
Harker
Emma L
EL
Carswell
David R
DR
Carbery
D004952:Esters / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D004952:Esters; D011392:Proline; C072401:beta-proline