New enantiomerically enriched amino allyl- and allenylsilanes derived from naturally occurring amino acids
摘要:
Some enantiomerically enriched Z-amino allylsilanes and allenylsilanes have been obtained selectively through the synthetic elaboration of naturally occurring amino acids. Fluorodesilylation with Selectfluor (R) has been proved as an easy way for preparing allylic fluorides bearing an amino or an amino acid moiety on the lateral chain. In particular, a new unsaturated fluorinated amino acid has been obtained, albeit as a diastereomeric mixture. (C) 2009 Elsevier Ltd. All rights reserved.
The synthesis of various types of optically active α-(allenylsilane-containing)glycines via a chirality-transferring ester-enolate Claisen rearrangement of α-acyloxy-α-alkynylsilanes is described. The conversion of the rearranged products into the optically active silicon-free α-(allenyl)- and α-substituted-α-(allenyl)glycines was achieved by the removal of the Me2PhSi- or TMS group from the allene