NHC-catalyzed cascade reaction between β-methyl enals and dienones for quick construction of complex multicyclic lactones

NHC-catalyzed cascade reaction between β-methyl enals and dienones for quick construction of complex multicyclic lactones

A NHC-promoted cascade reaction between β-methyl enal and dienone is developed for quick access to multicyclic lactone molecules bearing quaternary chiral carbon centers. Our study constitutes the first 1,6-addition of the acylazolium vinyl enolate γ-carbon via NHC catalysis and provides rapid acces...

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Main Authors: Sun, Jun, Xu, Jun, Nie, Guihua, Jin, Zhichao, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2021
Subjects:
Science::Chemistry
Lactones
Molecules
Online Access:https://hdl.handle.net/10356/148642
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1486422023-02-28T19:55:38Z NHC-catalyzed cascade reaction between β-methyl enals and dienones for quick construction of complex multicyclic lactones Sun, Jun Xu, Jun Nie, Guihua Jin, Zhichao Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry Lactones Molecules A NHC-promoted cascade reaction between β-methyl enal and dienone is developed for quick access to multicyclic lactone molecules bearing quaternary chiral carbon centers. Our study constitutes the first 1,6-addition of the acylazolium vinyl enolate γ-carbon via NHC catalysis and provides rapid access to complex lactone molecules that are otherwise difficult to prepare. The structurally sophisticated lactone products bearing up to four fused ring structures are afforded in up to quantitative yields with good to excellent enantioselectivities. Ministry of Education (MOE) National Research Foundation (NRF) Accepted version The authors acknowledge financial support from the National Natural Science Foundation of China (21772029, 21801051, and 21961006), the National Key Technologies R&D Program (2014BAD23B01), The 10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649), the Guizhou Province Returned Oversea Student Science and Technology Activity Program [(2014)-2], the Science and Technology Department of Guizhou Province ([2018]2802 and [2019]1020), the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023), Guizhou University, the Guizhou Province First-Class Disciplines Project [(Yiliu Xueke Jianshe Xiangmu)-GNYL(2017)008], the Open Fund of Guizhou Key Laboratory of Miao Medicine (QMYY [2017] 101), Guizhou University of Traditional Chinese Medicine, the Singapore National Research Foundation (NRF-NRFI2016- 06), the Ministry of Education of Singapore (RG 1/18, RG 5/ 19, MOE2018-T3-1-003), A*STAR Individual Research Grants (A1783c0008 and A1783c0010), the GSK-EDB Trust Fund, a Nanyang Research Award Grant, and Nanyang Technological University. 2021-05-18T08:02:31Z 2021-05-18T08:02:31Z 2020 Journal Article Sun, J., Xu, J., Nie, G., Jin, Z. & Chi, R. Y. (2020). NHC-catalyzed cascade reaction between β-methyl enals and dienones for quick construction of complex multicyclic lactones. Organic Letters, 22(7), 2595-2599. https://dx.doi.org/10.1021/acs.orglett.0c00533 1523-7052 0000-0003-3003-6437 0000-0003-0573-257X https://hdl.handle.net/10356/148642 10.1021/acs.orglett.0c00533 32191485 2-s2.0-85082340598 7 22 2595 2599 en Organic Letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.0c00533 application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Lactones
Molecules
spellingShingle Science::Chemistry
Lactones
Molecules
Sun, Jun
Xu, Jun
Nie, Guihua
Jin, Zhichao
Chi, Robin Yonggui
NHC-catalyzed cascade reaction between β-methyl enals and dienones for quick construction of complex multicyclic lactones
description A NHC-promoted cascade reaction between β-methyl enal and dienone is developed for quick access to multicyclic lactone molecules bearing quaternary chiral carbon centers. Our study constitutes the first 1,6-addition of the acylazolium vinyl enolate γ-carbon via NHC catalysis and provides rapid access to complex lactone molecules that are otherwise difficult to prepare. The structurally sophisticated lactone products bearing up to four fused ring structures are afforded in up to quantitative yields with good to excellent enantioselectivities.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Sun, Jun
Xu, Jun
Nie, Guihua
Jin, Zhichao
Chi, Robin Yonggui
format Article
author Sun, Jun
Xu, Jun
Nie, Guihua
Jin, Zhichao
Chi, Robin Yonggui
author_sort Sun, Jun
title NHC-catalyzed cascade reaction between β-methyl enals and dienones for quick construction of complex multicyclic lactones
title_short NHC-catalyzed cascade reaction between β-methyl enals and dienones for quick construction of complex multicyclic lactones
title_full NHC-catalyzed cascade reaction between β-methyl enals and dienones for quick construction of complex multicyclic lactones
title_fullStr NHC-catalyzed cascade reaction between β-methyl enals and dienones for quick construction of complex multicyclic lactones
title_full_unstemmed NHC-catalyzed cascade reaction between β-methyl enals and dienones for quick construction of complex multicyclic lactones
title_sort nhc-catalyzed cascade reaction between β-methyl enals and dienones for quick construction of complex multicyclic lactones
publishDate 2021
url https://hdl.handle.net/10356/148642
_version_ 1759853933511049216

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