1, 5-diaza-cis-decalins

Diaza-cis-decalin, the bicychc analogue of tetramethyl-ethylenedia-mine, shown in Scheme 6.58, is an interesting (chiral) ligand [185, 186]. Is there a problem with the possible bicyclization approach shown ... 

Scheme 6.58 Reductive amination in a bicyclization approach to 1,5-diaza-cis-decalin...

For another synthesis of 1,5-diaza-cis-decalin, consider anellation approaches starting, e.g., from lysine. 

Kozlowski and coworkers have reported an oxidative rearrangement of cis- and tran5-l,5-diazadecalins promoted by (diacetoxyiodo)benzene in aqueous solution. In a specific example, upon treatment with (diace-toxyiodo)benzene in aqueous NaOH, 1,5-diaza-c/x-decalin (28) undergoes oxidation along with fragmentation to yield the ring-expanded bislactam 29 (Scheme 6.13) [44]. 

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