Regioselective Synthesis of Multifunctional Allylic Amines; Access to Ambiphilic Aziridine Scaffolds

We describe, for the first time, a highly regioselective hydrosilylation of propargylic amines. The reaction utilizes a PtCl2/XantPhos catalyst system to deliver hydrosilanes across the alkyne to afford multifunctional allylic amines in high yields. The reaction is tolerant to a wide variety of func...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 23; no. 11; pp. 4463 - 4467
Main Authors Roberts, Dean D, McLaughlin, Mark G
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.06.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BRONSTED ACID
SUBSTITUTION
HYDROSILYLATION
SILICON
CHEMISTRY
CATALYST
LIGAND
Online AccessGet full text

Cover

More Information
Summary:We describe, for the first time, a highly regioselective hydrosilylation of propargylic amines. The reaction utilizes a PtCl2/XantPhos catalyst system to deliver hydrosilanes across the alkyne to afford multifunctional allylic amines in high yields. The reaction is tolerant to a wide variety of functional groups and provides high value intermediates with two distinct functional handles. The synthetic applicability of the reaction has been shown through the synthesis of diverse ambiphilic aziridines.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01398