Sequential Photocatalytic Reactions for the Diastereoselective Synthesis of Cyclobutane Scaffolds

Mark J. Deeprose; Martin Lowe; Adam Noble; Kevin I. Booker-milburn; Varinder K. Aggarwal

doi:10.1021/acs.orglett.1c03746

Sequential Photocatalytic Reactions for the Diastereoselective Synthesis of Cyclobutane Scaffolds

Mark J. Deeprose
, Martin Lowe
, Adam Noble
, Kevin I. Booker-milburn
, Varinder K. Aggarwal

Research output: Contribution to journal › Article (Academic Journal) › peer-review

25 Citations (Scopus)

198 Downloads (Pure)

Abstract

The synthesis of densely functionalized cyclobutanes containing all-carbon quaternary stereocenters in high regio- and diastereoselectivity remains synthetically challenging. Herein, we show that this can be achieved by using a sequential photocatalysis strategy, wherein 3-chloromaleimides undergo triplet sensitized [2 + 2] photocycloadditions with alkynes or alkenes followed by photoredox-catalyzed dechlorinative C–C bond forming reactions to install quaternary stereocenters. This allows the rapid assembly of structurally complex and sterically congested 3-azabicyclo[3.2.0]heptane scaffolds from readily available starting materials.

Original language	English
Pages (from-to)	137-141
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	1
Early online date	9 Dec 2021
DOIs	https://doi.org/10.1021/acs.orglett.1c03746
Publication status	Published - 14 Jan 2022

Bibliographical note

Funding Information:
We thank the NPIF, UCB, the University of Bristol, and the Bristol Chemical Synthesis Centre for Doctoral Training, EPSRC (EP/G036764/1). We thank Dawn White (University of Bristol) for helpful discussions and proofreading the manuscript.

Publisher Copyright:
© 2021 American Chemical Society

Research Groups and Themes

BCS and TECS CDTs
Organic & Biological

Access to Document

10.1021/acs.orglett.1c03746

Full-text PDF (accepted author manuscript)
This is the accepted author manuscript (AAM). The final published version (version of record) is available online via American Chemical Society at https://doi.org/10.1021/acs.orglett.1c03746. Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 897 KB

https://pubs.acs.org/doi/10.1021/acs.orglett.1c03746

Handle.net

Persistent link

Cite this

@article{c4800c7b001d4a5a89d7fa3055cdef3e,

title = "Sequential Photocatalytic Reactions for the Diastereoselective Synthesis of Cyclobutane Scaffolds",

abstract = "The synthesis of densely functionalized cyclobutanes containing all-carbon quaternary stereocenters in high regio- and diastereoselectivity remains synthetically challenging. Herein, we show that this can be achieved by using a sequential photocatalysis strategy, wherein 3-chloromaleimides undergo triplet sensitized [2 + 2] photocycloadditions with alkynes or alkenes followed by photoredox-catalyzed dechlorinative C–C bond forming reactions to install quaternary stereocenters. This allows the rapid assembly of structurally complex and sterically congested 3-azabicyclo[3.2.0]heptane scaffolds from readily available starting materials.",

author = "Deeprose, \{Mark J.\} and Martin Lowe and Adam Noble and Booker-milburn, \{Kevin I.\} and Aggarwal, \{Varinder K.\}",

note = "Funding Information: We thank the NPIF, UCB, the University of Bristol, and the Bristol Chemical Synthesis Centre for Doctoral Training, EPSRC (EP/G036764/1). We thank Dawn White (University of Bristol) for helpful discussions and proofreading the manuscript. Publisher Copyright: {\textcopyright} 2021 American Chemical Society",

year = "2022",

month = jan,

day = "14",

doi = "10.1021/acs.orglett.1c03746",

language = "English",

volume = "24",

pages = "137--141",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Sequential Photocatalytic Reactions for the Diastereoselective Synthesis of Cyclobutane Scaffolds

AU - Deeprose, Mark J.

AU - Lowe, Martin

AU - Noble, Adam

AU - Booker-milburn, Kevin I.

AU - Aggarwal, Varinder K.

N1 - Funding Information: We thank the NPIF, UCB, the University of Bristol, and the Bristol Chemical Synthesis Centre for Doctoral Training, EPSRC (EP/G036764/1). We thank Dawn White (University of Bristol) for helpful discussions and proofreading the manuscript. Publisher Copyright: © 2021 American Chemical Society

PY - 2022/1/14

Y1 - 2022/1/14

N2 - The synthesis of densely functionalized cyclobutanes containing all-carbon quaternary stereocenters in high regio- and diastereoselectivity remains synthetically challenging. Herein, we show that this can be achieved by using a sequential photocatalysis strategy, wherein 3-chloromaleimides undergo triplet sensitized [2 + 2] photocycloadditions with alkynes or alkenes followed by photoredox-catalyzed dechlorinative C–C bond forming reactions to install quaternary stereocenters. This allows the rapid assembly of structurally complex and sterically congested 3-azabicyclo[3.2.0]heptane scaffolds from readily available starting materials.

AB - The synthesis of densely functionalized cyclobutanes containing all-carbon quaternary stereocenters in high regio- and diastereoselectivity remains synthetically challenging. Herein, we show that this can be achieved by using a sequential photocatalysis strategy, wherein 3-chloromaleimides undergo triplet sensitized [2 + 2] photocycloadditions with alkynes or alkenes followed by photoredox-catalyzed dechlorinative C–C bond forming reactions to install quaternary stereocenters. This allows the rapid assembly of structurally complex and sterically congested 3-azabicyclo[3.2.0]heptane scaffolds from readily available starting materials.

U2 - 10.1021/acs.orglett.1c03746

DO - 10.1021/acs.orglett.1c03746

M3 - Article (Academic Journal)

C2 - 34882426

SN - 1523-7060

VL - 24

SP - 137

EP - 141

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Sequential Photocatalytic Reactions for the Diastereoselective Synthesis of Cyclobutane Scaffolds

Abstract

Bibliographical note

Research Groups and Themes

Access to Document

Handle.net

Fingerprint

Cite this