First Synthesis of Optically Pure Propargylic N-Hydroxylamines by Direct, Highly Diastereoselective Addition of Terminal Alkynes to Nitrones

First Synthesis of Optically Pure Propargylic N-Hydroxylamines by Direct, Highly Diastereoselective Addition of Terminal Alkynes to Nitrones

In situ generation of nucleophilic alkynilides by using substoichiometric amounts of Zn(OTf)2 (OTf = trifluoromethanesulfonate) followed by removal of the chiral auxiliary enables the direct use of a wide range of terminal acetylenes in the synthesis of optically pure propargylic N‐hydroxylamines (s...

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Veröffentlicht in:Angewandte Chemie International Edition 2002-08, Vol.41 (16), p.3054-3056
Hauptverfasser: Fässler, Roger, Frantz, Doug E., Oetiker, Jürg, Carreira, Erick M.
Format: Artikel
Sprache:eng
Schlagworte:
acetylides
diastereoselectivity
glycosylnitrones
hydroxylamines
zinc
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Zusammenfassung:In situ generation of nucleophilic alkynilides by using substoichiometric amounts of Zn(OTf)2 (OTf = trifluoromethanesulfonate) followed by removal of the chiral auxiliary enables the direct use of a wide range of terminal acetylenes in the synthesis of optically pure propargylic N‐hydroxylamines (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20020816)41:16<3054::AID-ANIE3054>3.0.CO;2-B