Development of the Ireland-Claisen rearrangement of alkoxy- and aryloxy-substituted allyl glycinates.
The Ireland-Claisen rearrangement of 3-alkoxy- and 3-aryloxy-substituted allyl glycinates is presented. This [3,3]-sigmatropic rearrangement route offers direct access to syn β-alkoxy and β-aryloxy α-amino acid systems. In particular, N,N-diboc glycine esters rearrange with excellent diastereoselectivities (dr > 25:1). The synthesis of substrates, rearrangement optimization, and a discussion of stereoselection are presented.
Tellam
James P
JP
Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, United Kingdom.
Carbery
David R
DR
D000438:Alcohols / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000438:Alcohols; D000596:Amino Acids; C059688:alkoxyl radical; D005998:Glycine