Heteroatom-Facilitated Lithiations of N-Methyl-N-(trimethylsilyl)methyl-benzylamine and Benzyl (Trimethylsilyl)methyl Ether with Butyllithium

Seiko MITSUI; Kiyotaka MARUMO; Sumie ANDO-INOUE; Hideo KATO; Yosiro SATO

doi:10.1248/cpb.41.2195

Seiko MITSUI, Kiyotaka MARUMO, Sumie ANDO-INOUE, Hideo KATO, Yosiro SATO

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Keywords: lithiation, chelation, organosilicon compound, heteroatom-facilitated lithiation silylmethylamine, silylmethyl ether

JOURNAL FREE ACCESS

1993 Volume 41 Issue 12 Pages 2195-2196

DOI https://doi.org/10.1248/cpb.41.2195

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Abstract

Lithiation of the Si-methyl groups of N-methyl-N-[(trimethylsilyl)methyl]benzylamine (1) occurred in preference to ortho-lithiation of the benzyl group with butyllithium in ether. In a similar reaction with benzyl (trimethylsilyl)methyl ether (7), lithiation of the benzylic position competed with that of the Si-methyl groups.

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