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HONG, Seung Youn
분자활성 촉매반응 연구단
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Catalytic access to carbocation intermediates via nitrenoid transfer leading to allylic lactams

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Title
Catalytic access to carbocation intermediates via nitrenoid transfer leading to allylic lactams
Author(s)
Seung Youn Hong; Dongwook Kim; Sukbok Chang
Publication Date
2021-01
Journal
NATURE CATALYSIS, v.4, no.1, pp.79 - 88
Publisher
NATURE RESEARCH
Abstract
Carbocation intermediacy is postulated in numerous organic transformations and provides the foundation for retrosynthetic logics in chemical synthesis. Although a number of catalytic approaches are designed to generate transient carbocations under mild conditions, there is room for improvement in the context of selectivity control and synthetic utility. Here we present an approach that enables catalytic access to carbocation intermediates via metal-nitrenoid transfer into alkenes, which subsequently allows a regiocontrolled elimination reaction. Customized catalysts are capable of bypassing competing pathways of the reactive intermediates to furnish valuable allylic lactams with excellent regioselectivity. Mechanistic investigations suggest that the ligand plays a critical role as an internal base in the selectivity-determining proton transfer process. This protocol is broadly applicable for preparing both five- and the more challenging four-membered allylamides. The virtue of this platform is further demonstrated by achieving the enantioselective construction of gamma-lactams.
URI
https://pr.ibs.re.kr/handle/8788114/10112
DOI
10.1038/s41929-020-00558-x
ISSN
2520-1158
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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