Conformationally Driven 2- and 3-Photon Cascade Processes in the Stereoselective Photorearrangement of Pyrroles

Paul Koovits; Jonathan Knowles; Kevin Booker-Milburn

doi:10.1021/acs.orglett.6b02829

Conformationally Driven 2- and 3-Photon Cascade Processes in the Stereoselective Photorearrangement of Pyrroles

Paul Koovits, Jonathan Knowles, Kevin Booker-Milburn

Applied Sciences Department

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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 two-photon 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
Journal	Organic Letters
Volume	18
Issue number	21
Early online date	27 Oct 2016
DOIs	https://doi.org/10.1021/acs.orglett.6b02829
Publication status	Published - 4 Nov 2016

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10.1021/acs.orglett.6b02829

Org Lett 2016 - author acceptedAccepted author manuscript, 499 KB

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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 two-photon sequence to tricyclic imines and an unprecedented stereoselective three-photon sequence to azabicyclo[3.3.1]nonanes.",

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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 two-photon sequence to tricyclic imines and an unprecedented stereoselective three-photon sequence to azabicyclo[3.3.1]nonanes.

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DO - 10.1021/acs.orglett.6b02829

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JO - Organic Letters

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Conformationally Driven 2- and 3-Photon Cascade Processes in the Stereoselective Photorearrangement of Pyrroles

Abstract

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