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Synthesis 2018; 50(15): 2954-2967
DOI: 10.1055/s-0036-1589541
DOI: 10.1055/s-0036-1589541
special topic
Cascade Radical Cyclization to Vinylogous Carbonates/Carbamates for the Synthesis of Oxa- and Aza-Angular Triquinanes: Diastereoselectivity Depends on the Ring Size of Radical Precursor
We thank SERB, New Delhi, for financial support.Further Information
Publication History
Received: 10 June 2018
Accepted after revision: 03 July 2018
Publication Date:
11 July 2018 (online)
Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis
Dedicated to Professor Sambasivarao Kotha, IIT Bombay, on the occasion of his 60th birthday.
Abstract
An efficient strategy was developed for the stereoselective construction of oxa- and aza-angular triquinanes employing a cascade 5-exo-trig radical cyclization to vinylogous carbonates and carbamates. The radical precursors are readily prepared from 2-(hydroxymethyl)cyclopentenone/cyclohexenones. High diastereoselectivity is observed for the formation of angular oxa- and azatriquinanes. Diastereoselectivity drops when six-membered radical precursors are used. The strategy is found to be useful to incorporate synthetically challenging moieties such as spiroindoline, lactone-bearing, and uracil-fused angular triquinanes in a concise manner.
Key words
oxatriquinanes - azatriquinanes - vinylogous carbonates - vinylogous carbamates - cascade/tandem radical cyclization - stereoselective synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589541.
- Supporting Information
- CIF File
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For reviews, see:
Selected examples: Oxatriquinanes:
Azatriquinanes:
Reviews:
Reviews: