Alkyne aza-Prins cyclization of N-(hexa-3,5-diynyl)tosylamides with aldehydes using triflic acid and a binuclear aluminum complex

Naoko Kobayashi; Kazuma Kaneko; Sho Amemiya; Keiichi Noguchi; Masahiro Yamanaka; Akio Saito

doi:10.1039/c9cc03700d

Alkyne aza-Prins cyclization of N-(hexa-3,5-diynyl)tosylamides with aldehydes using triflic acid and a binuclear aluminum complex

Chem Commun (Camb). 2019 Jul 18;55(59):8619-8622. doi: 10.1039/c9cc03700d.

Authors

Naoko Kobayashi¹, Kazuma Kaneko², Sho Amemiya¹, Keiichi Noguchi³, Masahiro Yamanaka², Akio Saito¹

Affiliations

¹ Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan. akio-sai@cc.tuat.ac.jp.
² Department of Chemistry and Research Center for Smart Molecules, Rikkyo University, 3-34-1 Nishi-Ikebukuro, Toshima-ku, Tokyo 171-8501, Japan. myamanak@rikkyo.ac.jp.
³ Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Japan.

PMID: 31282518
DOI: 10.1039/c9cc03700d

Abstract

The alkyne aza-Prins cyclization of 3,5-diynyl amides and various aldehydes was developed using TfOH with/without (Me2AlO)2SO2. This method, which could be applied to homopropargyl amides, provides TfO-substituted pyrrolidines with E-selectivities and exclusive regioselectivities. This work represents a first example of the aza-Prins cyclization with the introduction of TfO groups.