Journal of the Chemical Society. Perkin Transactions 2 (2001) p. 1299 - 1304 (1996)
Update date:2022-09-26
Topics:
Abell, Andrew D.
Taylor, Jane M.
Oldham, Mark D.
The alkylation of (2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one 7 with diphenylmethyl bromoacetate proceeded with high diastereoselectivity, and the resulting product was hydrolysed to give [(2′R,4′5)-3′-benzoyl-4′-benzyl-5′-oxo-2′- phenyloxazolidin-4′-yl]acetic acid 9. The self-addition by-product (2R,45,1′S)-3-benzoyl-4-[benzoylamino(phenyl)methyl]-4-benzyl-2-phenyl-1, 3-oxazolidin-5-one 11 was also isolated. The structures of compound of 11 and the related self-addition products (2R,4S,1′S and 1′R)-3-benzoyl-4-[benzoylamino(phenyl)methyl]-4-isopropyl-2-phenyl-1,3- oxazolidin-5-one 20 and 21 were determined by X-ray crystallography. The mechanism of formation of the self-addition products is discussed.
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