Synthesis 2017; 49(18): 4199-4204
DOI: 10.1055/s-0036-1588436
special topic
© Georg Thieme Verlag Stuttgart · New York

Intramolecular Hydroalkoxylation/Reduction and Hydroamination/Reduction of Unactivated Alkynes Using a Silane–Iodine Catalytic System

Shoji Fujita, Masatoshi Shibuya*, Yoshihiko Yamamoto
  • Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho Chikusa, Nagoya, 464-8601, Japan   Email: m-shibu@ps.nagoya-u.ac.jp
Japan Society for the Promotion of Science�, Grant Number: 'JP16K08162'�, Japan Agency for Medical Research and Development��.
Further Information

Publication History

Received: 31 March 2017

Accepted after revision: 02 May 2017

Publication Date:
24 May 2017 (eFirst)

Published as part of the Special Topic Modern Cyclization Strategies in Synthesis

Abstract

A transition-metal-free silane–iodine catalytic system comprising I2 and Et3SiH promotes intramolecular hydroalkoxylation/reduction and hydroamination/reduction of unactivated alkynes. This system allows the reaction to proceed at room temperature affording 2,4- and 2,5-disubstituted pyrrolidines as well as a 2,3-disubstituted tetrahydrofuran with high diastereoselectivity.

Supporting Information