Helvetica chimica acta

Electrophilic Bromination of N??Acylated Cyclohex??3??en??1??amines: Synthesis of 7??Azanorbornanes

P Kapferer, A Vasella

Index: Kapferer, Peter; Vasella, Andrea Helvetica Chimica Acta, 2004 , vol. 87, # 11 p. 2764 - 2789

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Citation Number: 32

Abstract

Abstract The intramolecular bromo-amidation and the dibromination-cyclisation of the N- acylcyclohex-3-en-1-amines 4, 8, 9, 11, 13, 14, and 16 was studied in view of the synthesis of bicyclic amines that are of interest as building blocks and potential glycosidase inhibitors. The trifluoroacetamides 4, 9, and 14 reacted with N-bromosuccinimide (NBS) in AcOH to give dihydro-1, 3-oxazines in good yields. The stereoselectivity of the dibromination of the ...