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^*

^*Corresponding author for this work

Chemistry

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

30 Scopus citations

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 (US)
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
State	Published - Feb 20 2012

Keywords

Lewis bases
NMR spectroscopy
asymmetric catalysis
isothioureas
reaction mechanisms

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201102847

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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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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.",

keywords = "Lewis bases, NMR spectroscopy, asymmetric catalysis, isothioureas, reaction mechanisms",

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.}",

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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

T2 - 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 - 2012/2/20

Y1 - 2012/2/20

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.

KW - Lewis bases

KW - NMR spectroscopy

KW - asymmetric catalysis

KW - isothioureas

KW - reaction mechanisms

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JO - Chemistry - A European Journal

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ER -

Isothiourea-mediated asymmetric O- to C-carboxyl transfer of oxazolyl carbonates: Structure-selectivity profiles and mechanistic studies

Abstract

Keywords

ASJC Scopus subject areas

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