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Asymmetric synthesis of pre-protected alpha,alpha-disubstituted amino acids from tert-butanesulfinyl ketimines



Asymmetric synthesis of pre-protected alpha,alpha-disubstituted amino acids from tert-butanesulfinyl ketimines



Tetrahedron Letters 42(8): 1433-1436, 19 February



A method for the asymmetric synthesis of pre-protected alpha,alpha-disubstituted amino acids is described. 5-Methylfuryllithium is added into sulfinyl ketimines 1 in the presence of AlMe3 to afford the sulfinamides 2 in 75-97% yields and with diastereoselectivities ranging from 75:25 to 99:1. Subsequent oxidation with RuCl3/NaIO4 affords tert-butanesulfonyl (Bus)-protected alpha,alpha-disubstituted amino acids 3 in 62-69% yields. Bus-protected amino acids readily undergo amide bond formation, after which the Bus group can be removed with TfOH/CH2Cl2 to afford the free amine.

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Accession: 010214934

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