Conformationally Driven Two- and Three-Photon Cascade Processes in the Stereoselective Photorearrangement of Pyrroles

Paul Koovits; Jonathan Knowles; Kevin Booker-Milburn

doi:10.1021/acs.orglett.6b02829

Conformationally Driven Two- and Three-Photon Cascade Processes in the Stereoselective Photorearrangement of Pyrroles

Paul Koovits, Jonathan Knowles, Kevin Booker-Milburn

School of Chemistry

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

13 Citations (Scopus)

328 Downloads (Pure)

Abstract

A TBSO group has been shown to exert a high degree of stereocontrol during the two-photon photocycloaddition/rearrangement of N-butenylpyrroles to complex tricyclic aziridines. Moreover, this and other bulky groups have been shown to change the outcome of the reaction, promoting a new twophoton sequence to tricyclic imines and an unprecedented stereoselective three-photon sequence to azabicyclo[3.3.1]nonanes.

Original language	English
Pages (from-to)	5608-5611
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.6b02829
Publication status	Published - 27 Oct 2016

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10.1021/acs.orglett.6b02829

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This is the accepted author manuscript (AAM). The final published version (version of record) is available online via American Chemical Society at DOI: 10.1021/acs.orglett.6b02829. Please refer to any applicable terms of use of the publisher.
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Factory in a Fumehood.
Booker-Milburn, K. I. (Principal Investigator)
1/10/13 → 1/03/17
Project: Research
An Extraordinary Photochemical Reaction of Pyrrole - A New Tool for Molecular Complexity
Booker-Milburn, K. I. (Principal Investigator)
7/01/13 → 7/01/16
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research

Cite this

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title = "Conformationally Driven Two- and Three-Photon Cascade Processes in the Stereoselective Photorearrangement of Pyrroles",

abstract = "A TBSO group has been shown to exert a high degree of stereocontrol during the two-photon photocycloaddition/rearrangement of N-butenylpyrroles to complex tricyclic aziridines. Moreover, this and other bulky groups have been shown to change the outcome of the reaction, promoting a new twophoton sequence to tricyclic imines and an unprecedented stereoselective three-photon sequence to azabicyclo[3.3.1]nonanes.",

author = "Paul Koovits and Jonathan Knowles and Kevin Booker-Milburn",

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doi = "10.1021/acs.orglett.6b02829",

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journal = "Organic Letters",

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T1 - Conformationally Driven Two- and Three-Photon Cascade Processes in the Stereoselective Photorearrangement of Pyrroles

AU - Koovits, Paul

AU - Knowles, Jonathan

AU - Booker-Milburn, Kevin

PY - 2016/10/27

Y1 - 2016/10/27

N2 - A TBSO group has been shown to exert a high degree of stereocontrol during the two-photon photocycloaddition/rearrangement of N-butenylpyrroles to complex tricyclic aziridines. Moreover, this and other bulky groups have been shown to change the outcome of the reaction, promoting a new twophoton sequence to tricyclic imines and an unprecedented stereoselective three-photon sequence to azabicyclo[3.3.1]nonanes.

AB - A TBSO group has been shown to exert a high degree of stereocontrol during the two-photon photocycloaddition/rearrangement of N-butenylpyrroles to complex tricyclic aziridines. Moreover, this and other bulky groups have been shown to change the outcome of the reaction, promoting a new twophoton sequence to tricyclic imines and an unprecedented stereoselective three-photon sequence to azabicyclo[3.3.1]nonanes.

U2 - 10.1021/acs.orglett.6b02829

DO - 10.1021/acs.orglett.6b02829

M3 - Article (Academic Journal)

C2 - 27788011

SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Conformationally Driven Two- and Three-Photon Cascade Processes in the Stereoselective Photorearrangement of Pyrroles

Abstract

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Factory in a Fumehood.

An Extraordinary Photochemical Reaction of Pyrrole - A New Tool for Molecular Complexity

3-month Core Capability for Chemistry Research

Cite this