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Multicomponent Coupling Reaction and Intramolecular Nitrile Oxide–Alkyne Cycloaddition towards Isoxazolo[3,4]‐pyrrolizines

Multicomponent Coupling Reaction and Intramolecular Nitrile Oxide–Alkyne Cycloaddition towards... This study reports an efficient four‐step method to synthesize a series of new (4S,8aS)‐3,4‐diphenyl‐6,7,8,8a‐tetrahydro‐4H‐isoxazolo[3,4‐a]pyrrolizines. The first step involves a copper(II) acetylacetonate catalyzed three component coupling of aldehyde, (S)‐pyrrolidin‐2‐ylmethanol, and alkynes (A3 coupling) to form propargylamines (4 a–4 n). The coupling reaction is applicable to various aldehydes, amines, and alkynes and provides the propargylamines in good to excellent yields with excellent distereoselectivities. Products (4 a–4 n) were converted into aldehydes (5 a–5 n) by Swern oxidation, aldehydes (5 a–5 n) were reacted with hydroxyl amine hydrochloride to form aldoxime (6 a–6 n), respectively. Further aldoximes (6 a–6 n) underwent an intramolecular 1,3‐dipolar cycloaddition to form tricyclic‐fused isoxazoles (7 a–7 n). The 1,3‐dipolar cycloaddition reaction tolerates high structural diversity and generated desired products (7 a–7 n) in moderate to good yields and excellent diastereoselectivities. A proposed mechanism for synthesis of 7 a is reported. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Multicomponent Coupling Reaction and Intramolecular Nitrile Oxide–Alkyne Cycloaddition towards Isoxazolo[3,4]‐pyrrolizines

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References (120)

Publisher
Wiley
Copyright
© 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201600223
Publisher site
See Article on Publisher Site

Abstract

This study reports an efficient four‐step method to synthesize a series of new (4S,8aS)‐3,4‐diphenyl‐6,7,8,8a‐tetrahydro‐4H‐isoxazolo[3,4‐a]pyrrolizines. The first step involves a copper(II) acetylacetonate catalyzed three component coupling of aldehyde, (S)‐pyrrolidin‐2‐ylmethanol, and alkynes (A3 coupling) to form propargylamines (4 a–4 n). The coupling reaction is applicable to various aldehydes, amines, and alkynes and provides the propargylamines in good to excellent yields with excellent distereoselectivities. Products (4 a–4 n) were converted into aldehydes (5 a–5 n) by Swern oxidation, aldehydes (5 a–5 n) were reacted with hydroxyl amine hydrochloride to form aldoxime (6 a–6 n), respectively. Further aldoximes (6 a–6 n) underwent an intramolecular 1,3‐dipolar cycloaddition to form tricyclic‐fused isoxazoles (7 a–7 n). The 1,3‐dipolar cycloaddition reaction tolerates high structural diversity and generated desired products (7 a–7 n) in moderate to good yields and excellent diastereoselectivities. A proposed mechanism for synthesis of 7 a is reported.

Journal

Asian Journal of Organic ChemistryWiley

Published: Aug 1, 2016

Keywords: ; ; ; ;

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