Diastereoselective Homoallylation and bis-homoallylation of N-tertbutanesulfinyl Imines with Organomagnesium Compounds

Author(s): Ana Sirvent , Francisco Foubelo* .

Journal Name: Letters in Organic Chemistry

Volume 15 , Issue 5 , 2018

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Abstract:

The addition of but-3-enylmagnesium bromide and pent-4-enylmagnesium bromide to N-tert-butanesulfinyl aldimines in toluene as solvent proceeds with high diastereoselectivity to yield the corresponding products of homoallylation and bis-homoallylation, respectively. The reactions are diastereoselective, and the configuration of the sulfur atom of the sulfinyl group determined the stereochemical outcome. The reaction products are aminoalkene derivatives of potential synthetic interest as precursors of nitrogen containing heterocycles.

Keywords: Homoallylation, bis-homoallylation, diastereoselective addition, N-tert-butanesulfinyl imines, grignard reagents, heterocycles.

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Article Details

VOLUME: 15
ISSUE: 5
Year: 2018
Page: [345 - 348]
Pages: 4
DOI: 10.2174/1570178614666171130162244
Price: $58

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