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Isomerization of Chiral Non‐Racemic α‐Substituted Propargylic Amines to Terminal Acetylenes
Author(s) -
Blanchet Jérome,
Bonin Martine,
Micouin Laurent,
Husson HenriPhilippe
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200208)2002:15<2598::aid-ejoc2598>3.0.co;2-v
Subject(s) - chemistry , epimer , isomerization , propargyl , oxidative cleavage , stereochemistry , alkyne , primary (astronomy) , organic chemistry , medicinal chemistry , catalysis , physics , astronomy
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. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)