Redox Isomerization/(3+2) Allenoate Annulation by Auto-Tandem Phosphine Catalysis

Jeremy T. Maddigan-Wyatt; Mitchell T. Blyth; Jhi Ametovski; Michelle L. Coote; Joel F. Hooper; David W. Lupton

doi:10.1002/chem.202103224

Redox Isomerization/(3+2) Allenoate Annulation by Auto-Tandem Phosphine Catalysis

Jeremy T. Maddigan-Wyatt, Mitchell T. Blyth, Jhi Ametovski, Michelle L. Coote, Joel F. Hooper, David W. Lupton

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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Abstract

A phosphine-catalyzed approach to pyrrolines has been developed that involves two mechanistically unlinked catalytic processes. The first involves the redox isomerization of amino crotonates to provide access to aliphatic tosyl imines, which then engage in a (3+2) annulation with various allenoates. The reaction shows generality, with 24 examples established, along with a low yielding and moderately enantioselective variant. Mechanistic studies indicate that the viability of the process is linked to the selection of catalysts with similar propensity to add to the two coupling partners.

Original language	English
Pages (from-to)	16232-16236
Number of pages	5
Journal	Chemistry - A European Journal
Volume	27
Issue number	65
DOIs	https://doi.org/10.1002/chem.202103224
Publication status	Published - 22 Nov 2021
Externally published	Yes

Bibliographical note

Funding Information:
The authors thank the Australian Research Council through the Discovery (DP200101448) and Laureate (FL170100041) programs for financial support, and the National Computational Infrastructure for supercomputing time.

Publisher Copyright:
© 2021 Wiley-VCH GmbH

Keywords

annulation
phosphine catalysis
redox isomerization
tandem catalysis

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10.1002/chem.202103224Licence: In Copyright

Author versionAccepted author manuscript, 1.21 MBLicence: In Copyright

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title = "Redox Isomerization/(3+2) Allenoate Annulation by Auto-Tandem Phosphine Catalysis",

abstract = "A phosphine-catalyzed approach to pyrrolines has been developed that involves two mechanistically unlinked catalytic processes. The first involves the redox isomerization of amino crotonates to provide access to aliphatic tosyl imines, which then engage in a (3+2) annulation with various allenoates. The reaction shows generality, with 24 examples established, along with a low yielding and moderately enantioselective variant. Mechanistic studies indicate that the viability of the process is linked to the selection of catalysts with similar propensity to add to the two coupling partners.",

keywords = "annulation, phosphine catalysis, redox isomerization, tandem catalysis",

author = "Maddigan-Wyatt, {Jeremy T.} and Blyth, {Mitchell T.} and Jhi Ametovski and Coote, {Michelle L.} and Hooper, {Joel F.} and Lupton, {David W.}",

note = "Funding Information: The authors thank the Australian Research Council through the Discovery (DP200101448) and Laureate (FL170100041) programs for financial support, and the National Computational Infrastructure for supercomputing time. Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

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AU - Maddigan-Wyatt, Jeremy T.

AU - Blyth, Mitchell T.

AU - Ametovski, Jhi

AU - Coote, Michelle L.

AU - Hooper, Joel F.

AU - Lupton, David W.

N1 - Funding Information: The authors thank the Australian Research Council through the Discovery (DP200101448) and Laureate (FL170100041) programs for financial support, and the National Computational Infrastructure for supercomputing time. Publisher Copyright: © 2021 Wiley-VCH GmbH

PY - 2021/11/22

Y1 - 2021/11/22

N2 - A phosphine-catalyzed approach to pyrrolines has been developed that involves two mechanistically unlinked catalytic processes. The first involves the redox isomerization of amino crotonates to provide access to aliphatic tosyl imines, which then engage in a (3+2) annulation with various allenoates. The reaction shows generality, with 24 examples established, along with a low yielding and moderately enantioselective variant. Mechanistic studies indicate that the viability of the process is linked to the selection of catalysts with similar propensity to add to the two coupling partners.

AB - A phosphine-catalyzed approach to pyrrolines has been developed that involves two mechanistically unlinked catalytic processes. The first involves the redox isomerization of amino crotonates to provide access to aliphatic tosyl imines, which then engage in a (3+2) annulation with various allenoates. The reaction shows generality, with 24 examples established, along with a low yielding and moderately enantioselective variant. Mechanistic studies indicate that the viability of the process is linked to the selection of catalysts with similar propensity to add to the two coupling partners.

KW - annulation

KW - phosphine catalysis

KW - redox isomerization

KW - tandem catalysis

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 65

ER -

Redox Isomerization/(3+2) Allenoate Annulation by Auto-Tandem Phosphine Catalysis

Abstract

Bibliographical note

Keywords

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