Non-peripherally substituted metallophthalocyanines catalyzed diastereoselective carbonyl-ylide reactions: Synthesis and DFT calculations

Fusun Seyma Gungor*, B. Sebnem Sesalan, Nurcan Senyurt Tuzun, Yilmaz Ozkilic, Olcay Anac

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Özet

Many catalysts are used to control the chemo-selectivity, diastereoselectivity, and enantioselectivity in carbenoid reactions. In this work, the [4 + 1] carbonyl-ylide reaction of dimethyl diazomalonate with α-ionone and the [3 + 2] carbonyl-ylide reaction of dimethyl diazomalonate with thiophene-2-carbaldehyde were chosen to obtain enriched diastereomeric products with the synthesized metallophthalocyanine compounds as catalysts. Four metallophthalocyanines (MPcs) including two neopenthoxy substituted and two novel fenchoxy substituted on non-peripheral positions of phthalocyanine ring were synthesized. Their catalytic activities were also compared with several common catalysts. Our results showed that in both reactions copper-Pc with neopentyl is the most effective catalyst to obtain diastereoselective results with diastereomeric product ratios of 30:70 and 10:90. DFT calculations also performed to explain the effect of the catalyst in diastereoselectivity. The calculations were in good agreement with the experimental results and assisted in understanding the selectivity.

Orijinal dilİngilizce
Makale numarası131892
DergiTetrahedron
Hacim80
DOI'lar
Yayın durumuYayınlandı - 29 Oca 2021

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Publisher Copyright:
© 2020 Elsevier Ltd

Finansman

Istanbul Technical University Scientific Research Fund supported this work (Project No: 39424 ). The authors acknowledge the National High Performance Computing Centre at ITU (grant no. 5004722017 ) for computational sources.

FinansörlerFinansör numarası
National High Performance Computing Centre
International Technological University5004722017

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