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C-H/C-C Functionalization Approach to N-Fused Heterocycles from Saturated Azacycles

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Title
C-H/C-C Functionalization Approach to N-Fused Heterocycles from Saturated Azacycles
Author(s)
Jin Su Ham; Bohyun Park; Mina Son; Jose B. Roque; Justin Jurczyk; Charles S. Yeung; Mu-Hyun Baik; Richmond Sarpong
Publication Date
2020-07
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.142, no.30, pp.13041 - 13050
Publisher
AMER CHEMICAL SOC
Abstract
© 2020 American Chemical Society Herein we report the synthesis of substituted indolizidines and related N-fused bicycles from simple saturated cyclic amines through sequential C-H and C-C bond functionalizations. Inspired by the Norrish-Yang Type II reaction, C-H functionalization of azacycles is achieved by forming alpha-hydroxy-beta-lactams from precursor alpha-ketoamide derivatives under mild, visible light conditions. Selective cleavage of the distal C(sp(2))-C(sp(3)) bond in alpha-hydroxy-beta-lactams using a Rh-complex leads to alpha-acyl intermediates which undergo sequential Rh-catalyzed decarbonylation, 1,4-addition to an electrophile, and aldol cyclization, to afford N-fused bicycles including indolizidines. Computational studies provide mechanistic insight into the observed positional selectivity of C-C cleavage, which depends strongly on the groups bound to Rh trans to the phosphine ligand
URI
https://pr.ibs.re.kr/handle/8788114/7748
DOI
10.1021/jacs.0c04278
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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