N-Boc-Amino Acid Mediated Morita-Baylis Hillman reaction of methylphenyl glyoxylate

Gamze Koz; Nejdet Coşkun

doi:10.38088/jise.1333127

EN

N-Boc-Amino Acid Mediated Morita-Baylis Hillman reaction of methylphenyl glyoxylate

Abstract

The organocatalyzed Morita-Baylis Hillman (MBH) reaction of α-keto esters is a challenging carbon-carbon bond-forming reaction. We developed a catalytic system for the MBH reaction of methylphenyl glyoxylate with methyl vinyl ketone in a polar aprotic solvent. We used N-Boc-L-pipecolinic acid as a proton transfer mediator and 4-dimethylaminopyridine as the tertiary amine catalyst. We obtained the MBH adduct with a 66% yield in 48h. We proposed a detailed reaction mechanism involving a transition state that includes the hydrogen transfer by the acid functional group of N-Boc-L-pipecolinic acid.

Keywords

Supporting Institution

Bursa Technical University, Scientific Research Fund

Project Number

182N02

Thanks

G. K. thanks TUBITAK for the fellowship (TUBITAK-2218). Bursa Technical University, Scientific Research Fund is gratefully acknowledged for financial support (Project No: 182N02).

References

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Details

Primary Language

English

Subjects

Organic Chemical Synthesis

Journal Section

Research Article

Authors

Gamze Koz ^*
0000-0003-3276-1413
Türkiye

Nejdet Coşkun
0000-0002-8464-9768
Türkiye

Early Pub Date

November 9, 2023

Publication Date

December 20, 2023

Submission Date

July 27, 2023

Acceptance Date

October 16, 2023

Published in Issue

Year 2023 Volume: 7 Number: 2

DOI

https://doi.org/10.38088/jise.1333127

IZ

https://izlik.org/JA29ZX93ZF

Cite

RIS / Bibtex

APA

Koz, G., & Coşkun, N. (2023). N-Boc-Amino Acid Mediated Morita-Baylis Hillman reaction of methylphenyl glyoxylate. Journal of Innovative Science and Engineering, 7(2), 160-166. https://doi.org/10.38088/jise.1333127

AMA

1.Koz G, Coşkun N. N-Boc-Amino Acid Mediated Morita-Baylis Hillman reaction of methylphenyl glyoxylate. JISE. 2023;7(2):160-166. doi:10.38088/jise.1333127

Chicago

Koz, Gamze, and Nejdet Coşkun. 2023. “N-Boc-Amino Acid Mediated Morita-Baylis Hillman Reaction of Methylphenyl Glyoxylate”. Journal of Innovative Science and Engineering 7 (2): 160-66. https://doi.org/10.38088/jise.1333127.

EndNote

Koz G, Coşkun N (December 1, 2023) N-Boc-Amino Acid Mediated Morita-Baylis Hillman reaction of methylphenyl glyoxylate. Journal of Innovative Science and Engineering 7 2 160–166.

IEEE

[1]G. Koz and N. Coşkun, “N-Boc-Amino Acid Mediated Morita-Baylis Hillman reaction of methylphenyl glyoxylate”, JISE, vol. 7, no. 2, pp. 160–166, Dec. 2023, doi: 10.38088/jise.1333127.

ISNAD

Koz, Gamze - Coşkun, Nejdet. “N-Boc-Amino Acid Mediated Morita-Baylis Hillman Reaction of Methylphenyl Glyoxylate”. Journal of Innovative Science and Engineering 7/2 (December 1, 2023): 160-166. https://doi.org/10.38088/jise.1333127.

JAMA

1.Koz G, Coşkun N. N-Boc-Amino Acid Mediated Morita-Baylis Hillman reaction of methylphenyl glyoxylate. JISE. 2023;7:160–166.

MLA

Koz, Gamze, and Nejdet Coşkun. “N-Boc-Amino Acid Mediated Morita-Baylis Hillman Reaction of Methylphenyl Glyoxylate”. Journal of Innovative Science and Engineering, vol. 7, no. 2, Dec. 2023, pp. 160-6, doi:10.38088/jise.1333127.

Vancouver

1.Gamze Koz, Nejdet Coşkun. N-Boc-Amino Acid Mediated Morita-Baylis Hillman reaction of methylphenyl glyoxylate. JISE. 2023 Dec. 1;7(2):160-6. doi:10.38088/jise.1333127

N-Boc-Amino Acid Mediated Morita-Baylis Hillman reaction of methylphenyl glyoxylate

Abstract

Keywords

Öz

Supporting Institution

Project Number

Thanks

References

Details

Primary Language

Subjects

Journal Section

Authors

Early Pub Date

Publication Date

Submission Date

Acceptance Date

Published in Issue

DOI

IZ

Cite