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Synthesis 2009(15): 2570-2578
DOI: 10.1055/s-0029-1216872
DOI: 10.1055/s-0029-1216872
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereoselective Synthesis of Unnatural β-Amino Acids from Nitroethane via 5,6-Dihydro-4H-1,2-oxazin-3-ylacetates
Further Information
Received
11 March 2009
Publication Date:
26 June 2009 (online)
Publication History
Publication Date:
26 June 2009 (online)
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Abstract
The reduction of easily available methyl 5,6-dihydro-4H-1,2-oxazin-3-ylacetates provides an efficient route to different diastereomerically pure unnatural β-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 β-amino acid esters with higher stereoselectivity than obtained with conventional catalytic hydrogenation.
Key words
β-amino acids - 5,6-dihydro-4H-1,2-oxazines - reduction - hydrogenation - nitroethane
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References
When hydrogenation of 2a-g is carried out under milder conditions, significant amounts of products of partial reduction are formed; see ref. 11.