Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent

Amy E. Shiely; Catherine N. Slattery; Alan Ford; Kevin S. Eccles; Simon E. Lawrence; Anita R. Maguire

doi:10.1039/c7ob00214a

Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent

Amy E. Shiely
, Catherine N. Slattery
, Alan Ford
, Kevin S. Eccles
, Simon E. Lawrence
, Anita R. Maguire

University College Cork

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

Abstract

Enantioselectivities in C-H insertion reactions, employing the copper-bis(oxazoline)-NaBARF catalyst system, leading to cyclopentanones are highest with sulfonyl substituents on the carbene carbon, and furthermore, the impact is enhanced by increased steric demand on the sulfonyl substituent (up to 91%ee). Enantioselective intramolecular C-H insertion reactions of α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones are reported for the first time.

Original language	English
Pages (from-to)	2609-2628
Number of pages	20
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	12
DOIs	https://doi.org/10.1039/c7ob00214a
Publication status	Published - 2017

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Shiely, A. E., Slattery, C. N., Ford, A., Eccles, K. S., Lawrence, S. E., & Maguire, A. R. (2017). Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent. Organic and Biomolecular Chemistry, 15(12), 2609-2628. https://doi.org/10.1039/c7ob00214a

@article{cb481904043a42498eca6387f91daadd,

title = "Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent",

abstract = "Enantioselectivities in C-H insertion reactions, employing the copper-bis(oxazoline)-NaBARF catalyst system, leading to cyclopentanones are highest with sulfonyl substituents on the carbene carbon, and furthermore, the impact is enhanced by increased steric demand on the sulfonyl substituent (up to 91\%ee). Enantioselective intramolecular C-H insertion reactions of α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones are reported for the first time.",

author = "Shiely, \{Amy E.\} and Slattery, \{Catherine N.\} and Alan Ford and Eccles, \{Kevin S.\} and Lawrence, \{Simon E.\} and Maguire, \{Anita R.\}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/c7ob00214a",

language = "English",

volume = "15",

pages = "2609--2628",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "12",

}

Shiely, AE, Slattery, CN, Ford, A, Eccles, KS, Lawrence, SE & Maguire, AR 2017, 'Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent', Organic and Biomolecular Chemistry, vol. 15, no. 12, pp. 2609-2628. https://doi.org/10.1039/c7ob00214a

Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent. / Shiely, Amy E.; Slattery, Catherine N.; Ford, Alan et al.
In: Organic and Biomolecular Chemistry, Vol. 15, No. 12, 2017, p. 2609-2628.

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

TY - JOUR

T1 - Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent

AU - Shiely, Amy E.

AU - Slattery, Catherine N.

AU - Ford, Alan

AU - Eccles, Kevin S.

AU - Lawrence, Simon E.

AU - Maguire, Anita R.

PY - 2017

Y1 - 2017

N2 - Enantioselectivities in C-H insertion reactions, employing the copper-bis(oxazoline)-NaBARF catalyst system, leading to cyclopentanones are highest with sulfonyl substituents on the carbene carbon, and furthermore, the impact is enhanced by increased steric demand on the sulfonyl substituent (up to 91%ee). Enantioselective intramolecular C-H insertion reactions of α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones are reported for the first time.

AB - Enantioselectivities in C-H insertion reactions, employing the copper-bis(oxazoline)-NaBARF catalyst system, leading to cyclopentanones are highest with sulfonyl substituents on the carbene carbon, and furthermore, the impact is enhanced by increased steric demand on the sulfonyl substituent (up to 91%ee). Enantioselective intramolecular C-H insertion reactions of α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones are reported for the first time.

UR - https://www.scopus.com/pages/publications/85016140779

U2 - 10.1039/c7ob00214a

DO - 10.1039/c7ob00214a

M3 - Article

C2 - 28267185

AN - SCOPUS:85016140779

SN - 1477-0520

VL - 15

SP - 2609

EP - 2628

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 12

ER -

Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent

Abstract

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