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Synthesis 2006(19): 3199-3208
DOI: 10.1055/s-2006-950226
DOI: 10.1055/s-2006-950226
PAPER
© Georg Thieme Verlag Stuttgart · New York
Phosphorus-Derived Chiral Auxiliaries for α-Alkylation of Secondary Amines by Anodic Oxidation
Further Information
Received
23 March 2006
Publication Date:
04 September 2006 (online)
Publication History
Publication Date:
04 September 2006 (online)
Abstract
Chiral phosphorus-based structures were investigated as N-activating groups for anodic oxidation and as chiral inductors. This first study presents the results obtained for pyrrolidine, with allyltrimethylsilane as a standard nucleophile. The methoxylated compounds were obtained in excellent yields (82-98%). The diastereoselectivity of the alkylation step (18-66%) is discussed with regard to the chiral auxiliary.
Key words
chiral auxiliaries - phosphorus derivatives - diastereoselective alkylation - secondary amines - pyrrolidines
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