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Carbonyl anti-(α-Amino)allylation via Ruthenium Catalyzed Hydrogen Autotransfer: Use of an Acetylenic Pyrrole as an Allylmetal Pronucleophile

Author:
Zhang, Wandi, Chen, Weijie, Xiao, Hongde, Krische, Michael J.
Source:
Organic letters 2017 v.19 no.18 pp. 4876-4879
ISSN:
1523-7052
Subject:
Lewis bases, aldehydes, alkynes, allene, allylation, catalytic activity, chemical structure, diastereoselectivity, hydrogen, isomerization, isopropyl alcohol, ruthenium
Abstract:
A single ruthenium complex catalyzes two discrete transformations resulting in the net conversion of an acetylenic pyrrole and alcohols to products of carbonyl anti-(α-amino)allylation. An initial catalytic process enables isomerization of an alkyne to a kinetically more reactive allene. A second catalytic process promotes alcohol-to-allene hydrogen transfer to form an aldehyde-allylruthenium pair that engages in regio- and diastereoselective carbonyl addition. A related reductive coupling of aldehydes mediated by 2-propanol also is described. The present catalytic processes represent rare examples of the use of alkynes as nucleophilic allylmetal precursors.
Agid:
5803086