Catalytic Asymmetric Addition of Alkynylzinc Reagents to Nitrones

The catalytic asymmetric addition of alkynylzinc reagents, which were prepared in situ from dimethylzinc and 1-alkynes, to nitrones was achieved by utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active (R)-N-(α-substituted)propargylic hydroxylamines....

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Bibliographic Details
Published in:Chemistry letters 2007-01, Vol.36 (1), p.44-45
Main Authors: Konishi, Atsuko, Wei, Weilin, Kobayashi, Masato, Fujinami, Shuhei, Ukaji, Yutaka, Inomata, Katsuhiko
Format: Article
Language:English
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Summary:The catalytic asymmetric addition of alkynylzinc reagents, which were prepared in situ from dimethylzinc and 1-alkynes, to nitrones was achieved by utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active (R)-N-(α-substituted)propargylic hydroxylamines. By the addition of methylzinc salt of a product-like racemic hydroxylamine, enantioselectivity of the N-propargylic hydroxylamines was enhanced up to 96% ee.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2007.44