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Synthesis of Boronic Ester γ‐Lactam Building Blocks

Rodgers, George ; Wilson, Ellen J. LU orcid ; Robertson, Craig C. ; Cox, Daniel J. and Partridge, Benjamin M. (2021) In Advanced Synthesis & Catalysis 363(9). p.2392-2395
Abstract
Saturated heterocycles are found widely in biologically active compounds such as medicinal drugs and agrochemicals. However, boronic acid-derived building blocks for these structures have limited availability, particularly in comparison to heteroaromatic boronic acids. We report the preparation of boronic ester γ-lactams through a Cu-catalysed conjugate borylation-cyclisation protocol. Using a chiral catalyst, this can be performed in high enantioselectivity. Exploration of the further transformations of these reagents suggest that the boronic esters have much potential as chemical building blocks.
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author
; ; ; and
publishing date
type
Contribution to journal
publication status
published
subject
in
Advanced Synthesis & Catalysis
volume
363
issue
9
pages
4 pages
publisher
John Wiley & Sons Inc.
external identifiers
  • scopus:85097604216
ISSN
1615-4169
DOI
10.1002/adsc.202001339
language
English
LU publication?
no
id
55a65f07-6bf5-4571-bd9d-0d5f251f7bbe
date added to LUP
2024-06-17 13:36:03
date last changed
2024-06-18 04:02:41
@article{55a65f07-6bf5-4571-bd9d-0d5f251f7bbe,
  abstract     = {{Saturated heterocycles are found widely in biologically active compounds such as medicinal drugs and agrochemicals. However, boronic acid-derived building blocks for these structures have limited availability, particularly in comparison to heteroaromatic boronic acids. We report the preparation of boronic ester γ-lactams through a Cu-catalysed conjugate borylation-cyclisation protocol. Using a chiral catalyst, this can be performed in high enantioselectivity. Exploration of the further transformations of these reagents suggest that the boronic esters have much potential as chemical building blocks.}},
  author       = {{Rodgers, George and Wilson, Ellen J. and Robertson, Craig C. and Cox, Daniel J. and Partridge, Benjamin M.}},
  issn         = {{1615-4169}},
  language     = {{eng}},
  month        = {{04}},
  number       = {{9}},
  pages        = {{2392--2395}},
  publisher    = {{John Wiley & Sons Inc.}},
  series       = {{Advanced Synthesis & Catalysis}},
  title        = {{Synthesis of Boronic Ester γ‐Lactam Building Blocks}},
  url          = {{http://dx.doi.org/10.1002/adsc.202001339}},
  doi          = {{10.1002/adsc.202001339}},
  volume       = {{363}},
  year         = {{2021}},
}