A scope of chiral cyclopropane of diazo acetoxy acetone with styrene derivatives, diazo acetoxy acetone derivatives with styrene catalyzed by p-nitro- Ru(ii)-diphenyl-Pheox
Vol. 132 No. 1C (2023), Original Article
Vol. 132 No. 1C (2023)

A scope of chiral cyclopropane of diazo acetoxy acetone with styrene derivatives, diazo acetoxy acetone derivatives with styrene catalyzed by p-nitro- Ru(ii)-diphenyl-Pheox

Original Article
https://doi.org/10.26459/hueunijns.v132i1C.7126
Published 2023-09-30
Le Thi Loan Chi*
University of Medicine and Pharmacy, Hue University, 6 Ngo Quyen St., Hue, Vietnam
Seiji Iwasa
Toyohashi University of Technology, Toyohashi, Aichi, Japan
PDF (Vietnamese)

Keywords

p-nitro-Ru(II)-diphenyl-Pheox
tổng hợp bất đối xứng
diazo ketone
phản ứng tạo sản phẩm đối quang cyclopropan
Ru(II)-Pheox p-nitro-Ru(II)-diphenyl-Pheox
asymmetric chemistry
Ru(II)-Pheox catalysts
diazo ketones
asymmetric cyclopropanation

How to Cite

1.
Lê TLC, Iwasa S. A scope of chiral cyclopropane of diazo acetoxy acetone with styrene derivatives, diazo acetoxy acetone derivatives with styrene catalyzed by p-nitro- Ru(ii)-diphenyl-Pheox . hueuni-jns [Internet]. 2023Sep.30 [cited 2024Jun.26];132(1C):99-113. Available from: https://jos.hueuni.edu.vn/index.php/hujos-ns/article/view/7126
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Abstract

In the publication about "The optimization on catalytic asymmetric intermolecular cyclopropanation of diazo acetoxy acetone and styrene by using p-nitro-Ru(II)-diphenyl-Pheox complex”, we presented the asymmetric cyclopropanation of diazo acetoxy acetone and styrene catalyzed by the asymmetric complex p-nitro-Ru-diphenyl-Pheox. This procedure has also been optimized under suitable solvent and temperature conditions and the products were achieved with high yields, excellent diastereoselectivity >99:1, and high enantioselectivity up to 95%. It is the first published result, demonstrating the effectiveness of this catalyst in the production of cyclopropane enantiomers. Additionally, this study provides sufficient evidence on how cyclopropane enantiomers are formed and how preferential trans products are formed. We continue to expand our research in order to further verify the published mechanism as well as expand the substrates that can be used to create highly selective cyclopropane enantiomers. Using p-nitro-Ru(II)-diphenyl-Pheox as a catalyzer. We investigated the reaction between diazo acetoxy acetone and styrene derivatives, as well as the reaction between diazo acetoxy acetone derivatives with styrene, the obtained products have high stereoselectivity (up to 99:1), with good yield (up to 92%), excellent enantioselectivity (up to 98% ee). This first published study contributes to the availability of many new and useful enriched cyclopropyl ketone products, found in natural and synthetic products of medicinal significance.

https://doi.org/10.26459/hueunijns.v132i1C.7126
PDF (Vietnamese)

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