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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-shibups.nagoya-u.ac.jp

S. Fujita, M. Shibuya, Y. Yamamoto, Synthesis, 2017, 49, 4199-4204.

DOI: 10.1055/s-0036-1588436 (free Supporting Information)


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Abstract

The use of Et3SiH and a catalytic amount of I2 enables transition-metal-free, intramolecular hydroalkoxylation/reduction and hydroamination/reduction of unactivated alkynes at room temperature to provide 2,4- and 2,5-disubstituted pyrrolidines as well as a 2,3-disubstituted tetrahydrofurans with high diastereoselectivity.

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Key Words

iodine, triethylsilane, hydroalkoxylation, hydroamination, pyrrolidines, tetrahydrofurans, unactivated alkynes


ID: J66-Y2017