Stereoselective Synthesis of Unnatural ?-Amino Acids from Nitroethane via 5,6-Dihydro-4H-1,2-oxazin-3-ylacetates.
- Resource Type
- Article
- Authors
- Sukhorukov, Alexey
- Source
- Synthesis. Aug2009, Vol. 2009 Issue 15, p2570-2578. 9p.
- Subject
- *AMINO acid synthesis
*ETHANES
*CHEMICAL reduction
*ACETATES
*CHEMICAL bonds
*HYDROGENATION
*CATALYSIS
*STEREOCHEMISTRY
- Language
- ISSN
- 0039-7881
The reduction of easily available methyl 5,6-dihydro-4 H-1,2-oxazin-3-ylacetates provides an efficient route to different diastereomerically pure unnatural ?-amino acids. A two-step protocol including reduction of the C=N bond of the initial oxazine with sodium cyanoborohydride during the first step and hydrogenation of the N-O bond during the second step produced the target ?-amino acid esters with higher stereoselectivity than obtained with conventional catalytic hydrogenation. [ABSTRACT FROM AUTHOR]