Isothiourea-Mediated Asymmetric O- to C-Carboxyl Transfer of Oxazolyl Carbonates: Structure-Selectivity Profiles and Mechanistic Studies

Caroline Joannesse; Craig P. Johnston; Louis C. Morrill; Philip A. Woods; Madeleine Kieffer; Tobias A. Nigst; Herbert Mayr; Tomas Lebl; Douglas Philp; Ryan A. Bragg; Andrew D. Smith

doi:10.1002/chem.201102847

Isothiourea-Mediated Asymmetric O- to C-Carboxyl Transfer of Oxazolyl Carbonates: Structure-Selectivity Profiles and Mechanistic Studies

Caroline Joannesse, Craig P. Johnston, Louis C. Morrill, Philip A. Woods, Madeleine Kieffer, Tobias A. Nigst, Herbert Mayr, Tomas Lebl, Douglas Philp, Ryan A. Bragg, Andrew D. Smith

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

Abstract

The structural motif within a series of tetrahydropyrimidine-based isothioureas necessary for generating high asymmetric induction in the asymmetric Steglich rearrangement of oxazolyl carbonates is fully explored, with crossover and dynamic 19F NMR experiments used to develop a mechanistic understanding of this transformation.

Original language	English
Pages (from-to)	2398-2408
Number of pages	11
Journal	Chemistry - A European Journal
Volume	18
Issue number	8
DOIs	https://doi.org/10.1002/chem.201102847
Publication status	Published - Feb 2012

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10.1002/chem.201102847

N-Heterocyclic Carbenes as Asymmetric: N-Heterocyclic Carbenes as Asymmetric Organocatalysts: Reaction Development
Smith, A. D. (PI)
EPSRC
1/04/07 → 30/09/10
Project: Standard

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Joannesse, C., Johnston, C. P., Morrill, L. C., Woods, P. A., Kieffer, M., Nigst, T. A., Mayr, H., Lebl, T., Philp, D., Bragg, R. A., & Smith, A. D. (2012). Isothiourea-Mediated Asymmetric O- to C-Carboxyl Transfer of Oxazolyl Carbonates: Structure-Selectivity Profiles and Mechanistic Studies. Chemistry - A European Journal, 18(8), 2398-2408. https://doi.org/10.1002/chem.201102847

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title = "Isothiourea-Mediated Asymmetric O- to C-Carboxyl Transfer of Oxazolyl Carbonates: Structure-Selectivity Profiles and Mechanistic Studies",

abstract = "The structural motif within a series of tetrahydropyrimidine-based isothioureas necessary for generating high asymmetric induction in the asymmetric Steglich rearrangement of oxazolyl carbonates is fully explored, with crossover and dynamic 19F NMR experiments used to develop a mechanistic understanding of this transformation.",

author = "Caroline Joannesse and Johnston, {Craig P.} and Morrill, {Louis C.} and Woods, {Philip A.} and Madeleine Kieffer and Nigst, {Tobias A.} and Herbert Mayr and Tomas Lebl and Douglas Philp and Bragg, {Ryan A.} and Smith, {Andrew D.}",

year = "2012",

month = feb,

doi = "10.1002/chem.201102847",

language = "English",

volume = "18",

pages = "2398--2408",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley & Sons, Ltd",

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Joannesse, C, Johnston, CP, Morrill, LC, Woods, PA, Kieffer, M, Nigst, TA, Mayr, H, Lebl, T , Philp, D, Bragg, RA & Smith, AD 2012, 'Isothiourea-Mediated Asymmetric O- to C-Carboxyl Transfer of Oxazolyl Carbonates: Structure-Selectivity Profiles and Mechanistic Studies', Chemistry - A European Journal, vol. 18, no. 8, pp. 2398-2408. https://doi.org/10.1002/chem.201102847

TY - JOUR

T1 - Isothiourea-Mediated Asymmetric O- to C-Carboxyl Transfer of Oxazolyl Carbonates: Structure-Selectivity Profiles and Mechanistic Studies

AU - Joannesse, Caroline

AU - Johnston, Craig P.

AU - Morrill, Louis C.

AU - Woods, Philip A.

AU - Kieffer, Madeleine

AU - Nigst, Tobias A.

AU - Mayr, Herbert

AU - Lebl, Tomas

AU - Philp, Douglas

AU - Bragg, Ryan A.

AU - Smith, Andrew D.

PY - 2012/2

Y1 - 2012/2

N2 - The structural motif within a series of tetrahydropyrimidine-based isothioureas necessary for generating high asymmetric induction in the asymmetric Steglich rearrangement of oxazolyl carbonates is fully explored, with crossover and dynamic 19F NMR experiments used to develop a mechanistic understanding of this transformation.

AB - The structural motif within a series of tetrahydropyrimidine-based isothioureas necessary for generating high asymmetric induction in the asymmetric Steglich rearrangement of oxazolyl carbonates is fully explored, with crossover and dynamic 19F NMR experiments used to develop a mechanistic understanding of this transformation.

U2 - 10.1002/chem.201102847

DO - 10.1002/chem.201102847

M3 - Article

SN - 0947-6539

VL - 18

SP - 2398

EP - 2408

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 8

ER -

Isothiourea-Mediated Asymmetric O- to C-Carboxyl Transfer of Oxazolyl Carbonates: Structure-Selectivity Profiles and Mechanistic Studies

Abstract

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N-Heterocyclic Carbenes as Asymmetric: N-Heterocyclic Carbenes as Asymmetric Organocatalysts: Reaction Development

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