1262217-03-7Relevant articles and documents
Synthesis of adamantylglycine using a diastereoselective grignard-to-nitrone addition
Baskakova, Alevtina,Frey, Wolfgang,Jaeger, Volker
, p. 3693 - 3699 (2010)
In contrast to amino acids with a bulky substituent like tert-leucine, adamantylglycine has so far received little attention. Here, a new, practical synthesis of adamantylglycine is described. This is based on a highly diastereoselective addition of adamantyl Grignard reagent to 2,3-O-cyclohexylideneglyceraldehyde N-benzylnitrone, mediated by the Lewis acid diethylaluminum chloride. Adamantylglycine is obtained from the nitrone in 6 steps and 28% yield as a crystalline hydrochloride with 0.5 methanol incorporated.