Ring‐Opening of  N‐tert ‐Butanesulfinylethynylaziridines with Lithium Tris(dimethylphenylsilyl)zincate: Stereoselective Access to 4‐Amino‐1‐allenylsilanes | Zendy

Bochatay Valentin N. | Zendy; Sanogo Youssouf | Zendy; Chemla Fabrice | Zendy; Ferreira Franck | Zendy; Jackowski Olivier | Zendy; PérezLuna Alejandro | Zendy

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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

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.

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