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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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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