Non??destructive Removal of the Bornanesultam Auxiliary in α??Substituted N??Acylbornane??10, 2??sultanis under Mild Conditions: An efficient synthesis of …

W Oppolzer, C Darcel, P Rochet, S Rosset…

Index: Oppolzer, Wolfgang; Darcel, Christophe; Rochet, Patrick; Rosset, Stephane; Brabander, Jef De Helvetica Chimica Acta, 1997 , vol. 80, # 5 p. 1319 - 1337

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Citation Number: 36

Abstract

Abstract α-Substituted N-acylbornane-10, 2-sultams 6, 9, and 10 can be converted into enantiomerically pure ketones 5. 13, and 14, respectively, via a two-step procedure involving a known mercaptolysis reaction followed by an [Fe (acac) 3]-mediated coupling of the resulting S-benzyl thioesters with Grignard reagents. Furthermore, enantiomerically pure aldehydes 23 can be obtained from α-substituted N-acylbornane-10, 2-sultams 6via a one ...