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Synthesis and applications of 3-methylene-4-(trifluoromethyl)azetidin-2-ones as building blocks for the preparation of mono- and spirocyclic 4-CF3-β-lactams

Hang Dao Thi, Barbara Danneels UGent, Tom Desmet UGent, Kristof Van Hecke UGent, Tuyen Van Nguyen and Matthias D'hooghe UGent (2016) ASIAN JOURNAL OF ORGANIC CHEMISTRY. 5(12). p.1480-1491
abstract
3-Methylene-4-(trifluoromethyl)azetidin-2-ones were efficiently prepared from the corresponding 3-oxo-4-trifluoromethyl--lactams and successfully evaluated as novel building blocks in organic synthesis. In particular, Michael additions, electrophilic additions, and cycloadditions were applied to allow easy access to a broad variety of stereodefined mono- and spirocyclic 4-CF3-beta-lactams as useful synthetic intermediates en route to a variety of biologically relevant CF3-functionalized target structures.
Please use this url to cite or link to this publication:
author
organization
alternative title
Synthesis and applications of 3-methylene-4-(trifluoromethyl)azetidin-2-ones as building blocks for the preparation of mono- and spirocyclic 4-CF3-beta-lactams
year
type
journalArticle (original)
publication status
published
subject
keyword
cycloadditions, electrophilic additions, fluorinated compounds, 3-methylene-4-(trifluoromethyl)azetidin-2-ones, Michael addition, spirocyclic lactams, ALKYLIDENE-BETA-LACTAMS, MEDICINAL CHEMISTRY, ALPHA-METHYLENE, STEREOSELECTIVE-SYNTHESIS, PHYLLOSTICTA-CIRSII, FLUORINE CHEMISTRY, AMINO ESTERS, AZETIDIN-2-ONES, CYCLOADDITIONS, ELIMINATION
journal title
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Asian J. Org. Chem.
volume
5
issue
12
pages
1480 - 1491
Web of Science type
Article
Web of Science id
000392527200011
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
2.788 (2016)
JCR rank
20/59 (2016)
JCR quartile
2 (2016)
ISSN
2193-5807
DOI
10.1002/ajoc.201600387
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
8500777
handle
http://hdl.handle.net/1854/LU-8500777
date created
2017-01-09 11:57:27
date last changed
2017-02-16 09:55:16
@article{8500777,
  abstract     = {3-Methylene-4-(trifluoromethyl)azetidin-2-ones were efficiently prepared from the corresponding 3-oxo-4-trifluoromethyl--lactams and successfully evaluated as novel building blocks in organic synthesis. In particular, Michael additions, electrophilic additions, and cycloadditions were applied to allow easy access to a broad variety of stereodefined mono- and spirocyclic 4-CF3-beta-lactams as useful synthetic intermediates en route to a variety of biologically relevant CF3-functionalized target structures.},
  author       = {Dao\hspace{.25em}Thi, Hang and Danneels, Barbara and Desmet, Tom and Van Hecke, Kristof and Van\hspace{.25em}Nguyen, Tuyen and D'hooghe, Matthias},
  issn         = {2193-5807},
  journal      = {ASIAN JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {cycloadditions,electrophilic additions,fluorinated compounds,3-methylene-4-(trifluoromethyl)azetidin-2-ones,Michael addition,spirocyclic lactams,ALKYLIDENE-BETA-LACTAMS,MEDICINAL CHEMISTRY,ALPHA-METHYLENE,STEREOSELECTIVE-SYNTHESIS,PHYLLOSTICTA-CIRSII,FLUORINE CHEMISTRY,AMINO ESTERS,AZETIDIN-2-ONES,CYCLOADDITIONS,ELIMINATION},
  language     = {eng},
  number       = {12},
  pages        = {1480--1491},
  title        = {Synthesis and applications of 3-methylene-4-(trifluoromethyl)azetidin-2-ones as building blocks for the preparation of mono- and spirocyclic 4-CF3-\ensuremath{\beta}-lactams},
  url          = {http://dx.doi.org/10.1002/ajoc.201600387},
  volume       = {5},
  year         = {2016},
}

Chicago
Dao Thi, Hang, Barbara Danneels, Tom Desmet, Kristof Van Hecke, Tuyen Van Nguyen, and Matthias D’hooghe. 2016. “Synthesis and Applications of 3-methylene-4-(trifluoromethyl)azetidin-2-ones as Building Blocks for the Preparation of Mono- and Spirocyclic 4-CF3-β-lactams.” Asian Journal of Organic Chemistry 5 (12): 1480–1491.
APA
Dao Thi, H., Danneels, B., Desmet, T., Van Hecke, K., Van Nguyen, T., & D’hooghe, M. (2016). Synthesis and applications of 3-methylene-4-(trifluoromethyl)azetidin-2-ones as building blocks for the preparation of mono- and spirocyclic 4-CF3-β-lactams. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 5(12), 1480–1491.
Vancouver
1.
Dao Thi H, Danneels B, Desmet T, Van Hecke K, Van Nguyen T, D’hooghe M. Synthesis and applications of 3-methylene-4-(trifluoromethyl)azetidin-2-ones as building blocks for the preparation of mono- and spirocyclic 4-CF3-β-lactams. ASIAN JOURNAL OF ORGANIC CHEMISTRY. 2016;5(12):1480–91.
MLA
Dao Thi, Hang, Barbara Danneels, Tom Desmet, et al. “Synthesis and Applications of 3-methylene-4-(trifluoromethyl)azetidin-2-ones as Building Blocks for the Preparation of Mono- and Spirocyclic 4-CF3-β-lactams.” ASIAN JOURNAL OF ORGANIC CHEMISTRY 5.12 (2016): 1480–1491. Print.