α-Iodo-α,β-Unsaturated Ketones as Vicinal Dielectrophiles: Their Reactions with Dinucleophiles Provide New Annulation Protocols for the Formation of Carbo- and Heterocyclic Ring Systems

Yu Chen; Michael G Gardiner; Ping Lan; Martin G Banwell

doi:10.1021/acs.joc.2c00383

α-Iodo-α,β-Unsaturated Ketones as Vicinal Dielectrophiles: Their Reactions with Dinucleophiles Provide New Annulation Protocols for the Formation of Carbo- and Heterocyclic Ring Systems

J Org Chem. 2022 May 6;87(9):6146-6160. doi: 10.1021/acs.joc.2c00383. Epub 2022 Apr 19.

Authors

Yu Chen^{1

2}, Michael G Gardiner³, Ping Lan^{1

2}, Martin G Banwell^{1

2}

Affiliations

¹ Institute of Advanced and Applied Chemical Synthesis, Jinan University, Guangzhou, Guangdong 510632, China.
² College of Pharmacy, Jinan University, Guangzhou, Guangdong 510632, China.
³ Research School of Chemistry, The Australian National University, Canberra, ACT 2601, Australia.

PMID: 35438488
DOI: 10.1021/acs.joc.2c00383

Abstract

α-Iodo-α,β-unsaturated ketones such as compound 1 serve as vicinal dielectrophiles and react with a range of dinucleophiles including pentane-2,4-dione and 1,3-indandione to produce [3 + 2]- and [2 + 1]-adducts such as 5 and 38, respectively. [4 + 2]- and [5 + 2]-cycloadducts have been obtained from compound 1 by related means. Preliminary studies reveal that α-iodinated α,β-unsaturated esters can also participate in at least some of these same processes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Charcoal*
Esters
Ketones*

Substances

Esters
Ketones
Charcoal