The diastereoselective synthesis of syn-α-alkyl α-hydroxy β-amino acids 4a-h was easily accomplished by reaction of the sodium dianion of the corresponding anti α-alkyl β-benzoylamino acid methyl esters with iodine. The intermediate α-iodo derivatives spontaneously afforded cis-oxazolines which, upon hydrolysis, provided the desired products, with diastereoselectivities up to 99:1.
A facile and stereocontrolled synthesis of syn-α-alkyl α-hydroxy β-amino acids / Nocioni A.M.; Papa C.; Tomasini C.. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 40:48(1999), pp. 8453-8456. [10.1016/S0040-4039(99)01772-4]
A facile and stereocontrolled synthesis of syn-α-alkyl α-hydroxy β-amino acids
Tomasini C.
1999
Abstract
The diastereoselective synthesis of syn-α-alkyl α-hydroxy β-amino acids 4a-h was easily accomplished by reaction of the sodium dianion of the corresponding anti α-alkyl β-benzoylamino acid methyl esters with iodine. The intermediate α-iodo derivatives spontaneously afforded cis-oxazolines which, upon hydrolysis, provided the desired products, with diastereoselectivities up to 99:1.File in questo prodotto:
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