Asymmetric alkylation or silylation of (S)-(−)-diphenylprolinol-derived α-silyl amide to synthesize optically pure α-monosilyl or bis(silyl) amides. Issue 26 (29th June 2016)

• Record Type: Journal Article
• Authors: Huang, Zhenggang; Gao, Lu; Song, Zhenlei
• Is Part Of: Tetrahedron letters. Volume 57:Issue 26(2016)
• Page Start: 2861
• Page End: 2864
• Publication Date: 2016-06-29
• Subjects: Chiral organosilane -- Asymmetric alkylation -- Geminal bis(silane); Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.05.058
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: ( S )-(−)-Diphenylprolinol is shown as an efficient auxiliary to ensure the high diastereoselectivity of alkylation. A range of optically pure chiral α-monosilyl amides were obtained in good yields with high diastereoselectivity. The approach is applicable to synthesize sterically congested chiral α-bis(silyl) amides. Abstract: Asymmetric alkylation or silylation of ( S )-(−)-diphenylprolinol-derived α-silyl amide has been developed to synthesize optically pure α-monosilyl or bis(silyl) amides in good yields with high diastereoselectivity.