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Ring‐Opening of N‐tert ‐Butanesulfinylethynylaziridines with Lithium Tris(dimethylphenylsilyl)zincate: Stereoselective Access to 4‐Amino‐1‐allenylsilanes
Author(s) -
Bochatay Valentin N.,
Sanogo Youssouf,
Chemla Fabrice,
Ferreira Franck,
Jackowski Olivier,
PérezLuna Alejandro
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500347
Subject(s) - zincate , stereoselectivity , chemistry , stereospecificity , lithium (medication) , ring (chemistry) , tris , nitrogen atom , stereochemistry , medicinal chemistry , catalysis , organic chemistry , biochemistry , medicine , zinc , endocrinology
Abstract The ring‐opening of N‐tert ‐butanesulfinylethynylaziridines with lithium tris(dimethylphenylsilyl)zincate is reported. The reaction is demonstrated to be both stereoselective and stereospecific and to proceed through an anti ‐S N 2′ process. Further deprotection of the nitrogen atom under mild conditions allows access to 4‐amino‐1‐(dimethylphenylsilyl)allenes with high yields and levels of stereoselectivity.