Chemical Communications p. 349 - 350 (1996)
Update date:2022-08-04
Topics:
Adams, David R.
Bailey, Patrick D.
Collier, Ian D.
Heffernan, John D.
Stokes, Stephen
The treatment of the N-benzyloxycarbonyl α-methyl esters of L-glutamine or L-asparagine with tert-butyl nitrite in refluxing acetonitrile results in selective hydrolysis of the amide group, giving optically pure Z-Glu-OMe (74%) or Z-Asp-OMe (88%); these are versatile chiral building blocks, and an efficient synthesis of cis-5-hydroxy-L-pipecolic acid from Z-Glu-OMe is described.
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