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