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| - Chemistry of N-Boc-N-tert-butylthiomethyl-Protectedα-Aminoorganostannanes: Diastereoselective Synthesis ofPrimary β-Amino Alcohols from α-Aminoorganostannanes
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| - Reaction of N-Boc-N-tert-butylthiomethyl-protected α-aminoorganostannanes with n-BuLi generatesthe corresponding α-aminoorganolithiums. Reactions of these organolithiums with aromaticaldehydes provides N-protected β-amino alcohols with diastereoselectivities up to >99:1 anti/syn;with aliphatic aldehydes, diastereoselectivities were typically 1:1. Diastereoselectivities varieddepending on the amount of aldehyde used. The N-protected β-amino alcohols could be deprotectedto primary amines by treatment with NaH to generate oxazolidinones followed by basic hydrolysis.Alternatively, treatment of the protected amino alcohols with acid furnished cyclic acetals thatcould be deprotected to primary amines with BF3·OEt2 and HS(CH2)3SH. Transmetalation ofenantiomerically enriched organostannanes with n-BuLi at −95 °C provided organolithiums that,although less configurationally stable than N-Boc-N-methyl-protected α-aminoorganolithiums, couldbe trapped with aldehydes with near-complete retention of configuration.
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