Studies towards C-3 functionalization of β-lactams using substituted allylsilanes

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• 作者：RENU THAPAR ; RESHMA ; S S BARI
• 关键词：Allylsilane ; β ; Lactams ; Lewis acid ; desulphurisation ; crotylsilane ; cinnamylsilane.
• 刊名：Journal of Chemical Sciences
• 出版年：2016
• 出版时间：November 2016
• 年：2016
• 卷：128
• 期：11
• 页码：1745-1753
• 全文大小：308 KB
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Chemistry
  
• 出版者：Springer India
• ISSN：0973-7103
• 卷排序：128

文摘

An effective and stereoselective synthesis of 3-(1′-methyl/phenylallyl)-3-phenylthio-β-lactams (3/4) using substituted allylsilane and Lewis acid is described. The reaction leads to the formation of a mixture of C-3 substituted allyl β-Lactams. However, these compounds on desulphurisation using tri-n-butyltinhydride and Raney Ni provide two separable diastereomers of the reduced product.Graphical AbstractIn the presence of TiCl₄, silanes such as crotylsilanes and cinnamylsilanes add efficiently at C-3 position of trans-3-chloro-3-phenylthio-β-lactams.