Literature DB >> 27381361

The first catalytic asymmetric cycloadditions of imines with an enolisable anhydride.

Sarah A Cronin1, Aarón Gutiérrez Collar, Sivaji Gundala, Claudio Cornaggia, Esther Torrente, Francesco Manoni, Astrid Botte, Brendan Twamley, Stephen J Connon.   

Abstract

The first catalytic, asymmetric reactions of imines with homophthalic anhydride to form disubstituted 3,4-dihydroisoquinolones are reported. The use of N-mesyl aldimines is key, as more basic imines undergo rapid uncatalysed reactions, while imines possessing larger N-sulphonyl substituents form lactams with lower ee.

Entities:  

Mesh:

Substances:

Year:  2016        PMID: 27381361     DOI: 10.1039/c6ob00048g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  4 in total

1.  Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins.

Authors:  Claire L Jarvis; Neyra M Jemal; Spencer Knapp; Daniel Seidel
Journal:  Org Biomol Chem       Date:  2018-06-13       Impact factor: 3.876

2.  Stereochemistry and Reactivity of the HPA-Imine Mannich Intermediate.

Authors:  Daniel Polyak; Ngan Phung; Jian Liu; Robert Barrows; Thomas J Emge; Spencer Knapp
Journal:  Tetrahedron Lett       Date:  2017-08-31       Impact factor: 2.415

3.  Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides.

Authors:  Stephen W Laws; Lucas C Moore; Michael J Di Maso; Q Nhu N Nguyen; Dean J Tantillo; Jared T Shaw
Journal:  Org Lett       Date:  2017-05-05       Impact factor: 6.005

4.  Development of a Cross-Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)-ABX.

Authors:  Jing-Kai Huang; Kak-Shan Shia
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-25       Impact factor: 15.336

  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.