Synthesis p. 622 - 623 (1989)
Update date:2022-08-11
Topics:
Wuts, Peter G. M.
Pruitt, Lynn E.
A new, efficient, cost-effective method for the preparation of the Evans'chiral auxiliary (4S)-4-isopropyl-2-oxazolidinone (4) is described.A Schotten-Baumann acylation of valine with phenyl carbonochloridate quantitatively affords the protected valine, which is then reduced with borane in tetrahydrofuran to give an alcohol.Cyclization with a catalytic amount of potassium tert-butoxide gives 4 in 81percent overall yield and in 41-43percent after crystallization from ethyl acetate/n-hexane.
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