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Concise enantio- and diastereoselective synthesis of α-hydroxy-α-methyl-β-amino acids

✍ Scribed by Rolf Roers; Gregory L Verdine

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
66 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Reported here is an efficient procedure for enantio-and diastereoselective synthesis of pure b-amino acids that display a tert-hydroxyl functionality in the a-position. Key steps include a catalytic asymmetric aldol reaction and a modified Curtius rearrangement to form oxazolidinone intermediates, which are chemoselectively opened to furnish N-protected a-hydroxy-amethyl-b-amino acids. A modified work-up procedure of the aldol reaction allows for recovery of up to 90% of bisoxazolinyl ligands from the catalysts.

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