A stereospecific access to allylic systems using rhodium (II)-vinyl carbenoid insertion into Si-H, OH, and NH bonds

…, L Parra-Rapado, D Planchenault…

Index: Bulugahapitiya, Priyadarshanie; Landais, Yannick; Parra-Rapado, Liliana; Planchenault, Denis; Weber, Valery Journal of Organic Chemistry, 1997 , vol. 62, # 6 p. 1630 - 1641

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Citation Number: 102

Abstract

Rhodium-catalyzed decomposition of α-vinyldiazoesters in the presence of silanes, alcohols, ethers, amines, and thiols have been shown to produce the corresponding α-silyl, α-hydroxy, α-alkoxy, α-amino, and α-thioalkoxy esters in generally good yield with a complete retention of the stereochemistry of the double bond of the diazo precursor. An extension of the process in homochiral series has also been devised using either a chiral ...