Stereocontrolled α-Alkylation of Oxime Ether Derived from Terpene: Efficient Synthesis of New Chiral γ- and δ-Amino Alcohols

Abstract The alkylation of (+)-nopinone oxime ether with various electrophiles afforded the corresponding adduct with a total stereoselectivity. Further reduction of the oxime ether afforded an easily access to new chiral γ-and δ-amino alcohols of high interest for catalysis and asymmetric synthesis...

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Bibliographic Details
Published in:Synlett 2008-07, Vol.2008 (11), p.1669-1672
Main Authors: Jennequin, Thomas, Labat, Stéphane, Toupet, Loïc, Caille, Jean-Claude, Mauduit, Marc
Format: Article
Language:English
Subjects:
Chemical Sciences
letter
Organic chemistry
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Summary:Abstract The alkylation of (+)-nopinone oxime ether with various electrophiles afforded the corresponding adduct with a total stereoselectivity. Further reduction of the oxime ether afforded an easily access to new chiral γ-and δ-amino alcohols of high interest for catalysis and asymmetric synthesis.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2008-1078492