Literature DB >> 23909824

Concise synthesis of (+)-allo-kainic acid via MgI2-mediated tandem aziridine ring opening-formal [3 + 2] cycloaddition.

Giada Arena1, C Chun Chen, Daniele Leonori, Varinder K Aggarwal.   

Abstract

3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.

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Year:  2013        PMID: 23909824     DOI: 10.1021/ol4020333

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Three-Dimensional Large-Scale Fused Silica Microfluidic Chips Enabled by Hybrid Laser Microfabrication for Continuous-Flow UV Photochemical Synthesis.

Authors:  Aodong Zhang; Jian Xu; Yucen Li; Ming Hu; Zijie Lin; Yunpeng Song; Jia Qi; Wei Chen; Zhaoxiang Liu; Ya Cheng
Journal:  Micromachines (Basel)       Date:  2022-03-30       Impact factor: 3.523

Review 2.  Nucleophilic ring opening reactions of aziridines.

Authors:  Rabia Akhtar; Syed Ali Raza Naqvi; Ameer Fawad Zahoor; Sameera Saleem
Journal:  Mol Divers       Date:  2018-05-04       Impact factor: 2.943

3.  Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides.

Authors:  Oleksandr Zhurakovskyi; Yunus E Türkmen; Lorenz E Löffler; Vijayalakshmi A Moorthie; C Chun Chen; Michael A Shaw; Mark R Crimmin; Marco Ferrara; Mushtaq Ahmad; Mehrnoosh Ostovar; Johnathan V Matlock; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-09       Impact factor: 15.336

4.  Phosphine-Promoted [4 + 3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3 + 3] and [4 + 3] Pathways.

Authors:  Honglei Liu; Yan Lin; Yan Zhao; Miaoren Xiao; Leijie Zhou; Qijun Wang; Cheng Zhang; Dongqi Wang; Ohyun Kwon; Hongchao Guo
Journal:  RSC Adv       Date:  2019-01-09       Impact factor: 4.036

  4 in total

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