Helvetica chimica acta

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

P Kapferer, A Vasella

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

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被引用次数: 32

摘要

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 ...