Synthesis of Enantiopure Spiro-isoxazolidine from stable Ketonitrones via [۳+۲] Cycloaddition in High pressure condition

سال انتشار: 1401
نوع سند: مقاله کنفرانسی
زبان: انگلیسی
مشاهده: 147

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شناسه ملی سند علمی:

CHCONFE04_019

تاریخ نمایه سازی: 20 بهمن 1401

چکیده مقاله:

Because of enantiopure spiro-isoxazolidine importance, an efficient system was advanced for them synthesis through an asymmetric ۱, ۳-dipolar cycloaddition reaction of N-Phenyl Acenaphthylen/Oxindole Nitrones and an optically active ۱, ۳-dipolarophile equipped with chiral auxiliary. The best result in diastereoselectivity was obtained by use of (S)-Oxazolidinone as chiral auxiliary. After the extensive investigations to find the best conditions for increasing the reactivity of stable keto-nitrones, it was found that in high-pressure condition, a favorable reactivity is obtained. Further, in order to improve the efficiency of the reaction, more active dipolarophile was synthesized and chiral spiro-isoxazolidine were synthesis in the high yield.

نویسندگان

Naeimeh Shahrestani

Faculty of Chemistry and Petroleum Sciences, Department of Organic Chemistry, Shahid Beheshti University, G.C., Tehran ۱۹۸۳۹۶۳۱۱۳, Iran.

Yasaman Tamaddon Abibiglue

Department of Medicinal Chemistry, School of Pharmacy, Tabriz University of Medicinal Sciences, Tabriz, Iran.

Khosrow Jadidi

Faculty of Chemistry and Petroleum Sciences, Department of Organic Chemistry, Shahid Beheshti University, G.C., Tehran ۱۹۸۳۹۶۳۱۱۳, Iran.

Behrouz Notash

Faculty of Chemistry and Petroleum Sciences, Department of Inorganic Chemistry, Shahid Beheshti University, Tehran ۱۹۸۳۹ ۶۹۴۱۱ (Iran)