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Article Dans Une Revue European Journal of Organic Chemistry Année : 2002

Isomerization of Chiral Non-Racemic α-Substituted Propargylic Amines to Terminal Acetylenes

Résumé

Various α‐substituted propargylamines, prepared in three steps from (R)‐phenylglycinol, are readily isomerized at 0 °C with KAPA to form terminal acetylenic amines, without any detectable epimerization of the chiral center, as already observed for propargyl alcohols. Enantiomerically pure primary α‐substituted alkynylamines can be easily obtained in two steps after removal of the ferrocenylmethyl protective group and oxidative cleavage of the chiral appendage.

Domaines

Chimie organique
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Dates et versions

hal-02185592 , version 1 (16-07-2019)

Identifiants

Citer

Jérôme Blanchet, Martine Bonin, Laurent Micouin, Henri-Philippe Husson. Isomerization of Chiral Non-Racemic α-Substituted Propargylic Amines to Terminal Acetylenes. European Journal of Organic Chemistry, 2002, 2002 (15), pp.2598-2602. ⟨10.1002/1099-0690(200208)2002:15<2598::AID-EJOC2598>3.0.CO;2-V⟩. ⟨hal-02185592⟩
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