Rebecca M. Maksymowicz

University of Oxford

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Stephen P. Fletcher

University of Oxford

Philippe M. C. Roth

Corning (United States)

Mireia Sidera

Vertex Pharmaceuticals (United Kingdom)

Andrew J. Bissette

Interscience Communications (United Kingdom)

Amber L. Thompson

University of Oxford

Eleanor E. Maciver

University of Oxford

Nancy Wilkinson

University of Oxford

Amanda C. Jones

Wake Forest University

Qian Peng

Nankai University

Robert S. Paton

Colorado State University

Cooperative Institutions

University of Oxford

University of Wisconsin–Madison

Science Oxford

Vertex Pharmaceuticals (United Kingdom)

Chulabhorn Hospital

Colorado State University

Oxford Research Group

Middle East Technical University

Ahi Evran University

Oxfam

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A Rapid Injection NMR Study of the Reaction of Organolithium Reagents with Esters, Amides, and Ketones

Organic Letters (2015)

Kristin Plessel Amanda C. Jones Daniel Wherritt Rebecca M. Maksymowicz EricT. Poweleit

Unexpectedly high rates of reaction between alkyllithium reagents and amides, compared to esters and ketones, were observed by Rapid Inject NMR and competition experiments. Spectroscopic investigations with 4-fluorophenyllithium (ArLi, mixture of monomer and dimer in THF) and a benzoate ester identified two reactive intermediates, a homodimer of the tetrahedral intermediate, stable below -100 °C, and a mixed dimer with ArLi. Direct formation of dimers suggested that the ArLi dimer may be the reactive aggregate rather than the usually more reactive monomer. In contrast, RINMR experiments with ketones demonstrated that the ArLi monomer was the reactive species.

Reactive intermediate

10.1021/acs.orglett.5b00650

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Citations (15)

Formation of Quaternary Centers by Copper‐Catalyzed Asymmetric Conjugate Addition of Alkylzirconium Reagents

Angewandte Chemie (2013)

Mireia Sidera Philippe M. C. Roth Rebecca M. Maksymowicz Stephen P. Fletcher

Leicht gemacht: In situ aus einfachen Alkenen erzeugte Alkylzirconocene führen in hoch enantioselektiven kupferkatalysierten 1,4-Additionen an trisubstituierte cyclische Enone zur Einführung quartärer Zentren. Die Reaktionen laufen bei Raumtemperatur ab und sind mit dem Vorliegen vieler funktioneller Gruppen vereinbar. Cp=Cyclopentadienyl, Tf=Trifluormethansulfonyl. As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Cyclopentadienyl complex

Conjugate

10.1002/ange.201303202

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Citations (13)

Hydrometallation-asymmetric conjugate addition: application to complex molecule synthesis

Chemical Communications (2012)

Rebecca M. Maksymowicz Philippe M. C. Roth Amber L. Thompson Stephen P. Fletcher

Copper catalysis allows alkyl zirconium species, generated in situ from alkenes, to undergo conjugate addition reactions. A hydrometallation-catalytic asymmetric 1,4-addition was used to synthesize either enantiomer of a natural product in one step from commercially available materials. Hydrometallation-addition sequences applied to steroids containing a cross-conjugated dienone or 1,6-acceptor give highly functionalized products.

Conjugate

Natural product

Acceptor

10.1039/c2cc37155c

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Citations (30)

ChemInform Abstract: Asymmetric Conjugate Addition of Alkylzirconium Reagents to α,β‐Unsaturated Lactones.

ChemInform (2014)

Eleanor E. Maciver Rebecca M. Maksymowicz Nancy Wilkinson Philippe M. C. Roth Stephen P. Fletcher

Abstract Product (‐)‐(VI) represents a late‐stage intermediate in the synthesis of the natural product mitsugashiwalactone.

Conjugate

Natural product

10.1002/chin.201450139

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Citations (0)

Asymmetric Conjugate Addition of Alkylzirconium Reagents to α,β-Unsaturated Lactones

Organic Letters (2014)

Eleanor E. Maciver Rebecca M. Maksymowicz Nancy Wilkinson Philippe M. C. Roth Stephen P. Fletcher

The asymmetric synthesis of β-substituted lactones by catalytic asymmetric conjugate addition of alkyl groups to α,β-unsaturated lactones is reported. The method uses alkylzirconium nucleophiles prepared in situ from alkenes and the Schwartz reagent. Enantioselective additions to 6- and 7-membered lactones proceed at rt, tolerate a wide variety of functional groups, and are readily scalable. The method was used in a formal asymmetric synthesis of mitsugashiwalactone.

Conjugate

Functional group

Formal synthesis

Addition reaction

10.1021/ol501292x

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Citations (26)

Formation of Quaternary Centers by Copper‐Catalyzed Asymmetric Conjugate Addition of Alkylzirconium Reagents

Angewandte Chemie International Edition (2013)

Mireia Sidera Philippe M. C. Roth Rebecca M. Maksymowicz Stephen P. Fletcher

Pure and simple: Alkylzirconocenes generated in situ from simple alkenes are used in highly enantioselective copper-catalyzed 1,4-addition reactions to trisubstituted cyclic enones to generate quaternary centers. These reactions operate at room temperature under a range of conditions and tolerate many functional groups. Cp=cyclopentadienyl, Tf=trifluoromethanesulfonyl. As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Conjugate

Cyclopentadienyl complex

10.1002/anie.201303202

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Citations (69)

ChemInform Abstract: Asymmetric Conjugate Additions and Allylic Alkylations Using Nucleophiles Generated by Hydro‐ or Carbometalation

ChemInform (2015)

Rebecca M. Maksymowicz Andrew J. Bissette Stephen P. Fletcher

Abstract Review: [65 refs.

Conjugate

10.1002/chin.201527277

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Citations (1)

CCDC 904095: Experimental Crystal Structure Determination

The Cambridge Structural Database (2013)

Rebecca M. Maksymowicz Philippe Roth A.L. Thompson Stephen P. Fletcher

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/cczbscf

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Citations (0)

ChemInform Abstract: Hydrometalation‐Asymmetric Conjugate Addition: Application to Complex Molecule Synthesis.

ChemInform (2013)

Rebecca M. Maksymowicz Philippe M. C. Roth Amber L. Thompson Stephen P. Fletcher

Abstract Cu‐catalysis allows alkyl zirconium species, generated in situ from alkenes, to undergo conjugate addition reactions.

Conjugate

10.1002/chin.201337171

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Citations (0)

ChemInform Abstract: Formation of Quaternary Centers by Copper‐Catalyzed Asymmetric Conjugate Addition of Alkylzirconium Reagents.

ChemInform (2013)

Mireia Sidera Philippe M. C. Roth Rebecca M. Maksymowicz Stephen P. Fletcher

Abstract A new, practical, highly enantioselective, and widely applicable method to prepare cyclic ketones bearing a quaternary stereogenic center is reported.

Stereocenter

Conjugate

Quaternary carbon

10.1002/chin.201351036

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Citations (0)