D. Dixon, S. Ley, F. Rodríguez
Nov 15, 2001
Citations
0
Influential Citations
21
Citations
Journal
ChemInform
Abstract
The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block undergoes efficient and highly diastereoselective lithium enolate Michael additions to α,β-unsaturated ketones, lactones, and nitro olefins. Subsequent deprotection of these Michael adducts gives α-hydroxy acids in very high yield. Hydrogenation of the nitro group in some of the adducts leads to γ-lactams, which can be easily converted into α-hydroxy-γ-amino acid derivatives.