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Synlett 2020; 31(17): 1691-1695
DOI: 10.1055/s-0040-1706750
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Regio- and Stereoselectivity in the 1,3-Dipolar Cycloaddition Reactions of Isoquinolinium Ylides with Cyclopenta[a]acenaphthylen-8-ones

Issa Yavari 
,
Parisa Ravaghi
,
Maryam Safaei
,
Jasmine Kayanian
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Abstract

A convenient regio- and diastereoselective synthesis of functionalized 5a,5b-dihydro-5H,13H-naphtho[1′′,8′′:4′,5′,6′]pentaleno[1′:3,4]pyrrolo[2,1-a]isoquinolin-5-ones via 1,3-dipolar cycloaddition reaction of 8H-cyclopenta[a]acenaphthylen-8-ones with carbonyl-stabilized isoquinolinium N-ylides, is described. Based on DFT calculations at b3lyp/6-311+g(d,p) level of theory, a nonconcerted mechanism is proposed to explain the regioselectivity of this reaction. The structure of a typical product was confirmed by X-ray crystallographic analysis.

Key words

regioselective synthesis - 1,3-dipolar cycloaddition - isoquinolinium ylide - cyclopentadienones - DFT calculations

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706750.
  • Supporting Information


Publication History

Received: 02 April 2020

Accepted after revision: 20 July 2020

Article published online:
11 August 2020

© 2020. Thieme. All rights reserved

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