TY - JOUR

T1 - Regioselective Synthesis of Multifunctional Allylic Amines; Access to Ambiphilic Aziridine Scaffolds

AU - Roberts, Dean D.

AU - McLaughlin, Mark G.

PY - 2021/6/4

Y1 - 2021/6/4

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.1c01398

DO - 10.1021/acs.orglett.1c01398

M3 - Journal article

VL - 23

SP - 4463

EP - 4467

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 11

ER -