Asymmetric Synthesis of Methyl α-Alkyl-valinates, -leucinates, and -isoleucinates Using (Cyclohexylidene-protected) D-Galactodialdehyde as Chiral Auxiliary
The Schiff bases 2 from protected D-galactodialdehyde 1 and methyl valinate, -leucinate, and -isoleucinate were diastereoselectively alkylated via the lithium derivatives 3.The asymmetric induction of the alkylation step varied from 23 to >95percent.Upon hydrolysis the alkylation products 5-7 furnished the optically active α-alkylated methyl (S)-valinates 8, -leucinates 10, and -isoleucinates 11.
Schoellkopf, Ulrich,Toelle, Reinhold,Egert, Ernst,Nieger, Martin
p. 399 - 405
(2007/10/02)
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