Reactions of secondary propargylamines with heteroallenes for the synthesis of diverse heterocycles

Vsevolod A Peshkov; Olga P Pereshivko; Anton A Nechaev; Anatoly A Peshkov; Erik V Van der Eycken

doi:10.1039/C7CS00065K

Reactions of secondary propargylamines with heteroallenes for the synthesis of diverse heterocycles

Chem Soc Rev. 2018 Jun 5;47(11):3861-3898. doi: 10.1039/C7CS00065K.

Authors

Vsevolod A Peshkov¹, Olga P Pereshivko¹, Anton A Nechaev², Anatoly A Peshkov³, Erik V Van der Eycken⁴

Affiliations

¹ College of Chemistry, Chemical Engineering and Materials Science, Dushu Lake Campus, Soochow University, Suzhou 215123, China. vsevolod@suda.edu.cn olga@suda.edu.cn.
² Laboratory of Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven, Belgium. erik.vandereycken@chem.kuleuven.be.
³ KAUST Catalysis Center, King Abdullah University of Science & Technology, Thuwal 23955-6900, Kingdom of Saudi Arabia.
⁴ Laboratory of Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven, Belgium. erik.vandereycken@chem.kuleuven.be and Peoples Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya street, Moscow, 117198, Russia.

PMID: 29546891
DOI: 10.1039/C7CS00065K

Abstract

This focused review aims to summarize recent developments in the processes involving additions of secondary propargylamines to various heteroallenes and subsequent transition metal-catalyzed or electrophile-mediated cyclizations. The utility of this convenient and tunable strategy spans from the carbon dioxide fixation and target-oriented synthesis of complex natural and biologically active products to the generation of extended synthetic libraries of diverse oxygen-, nitrogen- and sulfur-containing heterocycles. For comparative purposes, the analogous transformations of propargylic alcohols are also highlighted in this account.

Publication types

Review