Regio- and stereoselective synthesis of new diaminocyclopentanols

• Evgeni A. Larin,
• Valeri S. Kochubei and
• Yuri M. Atroshchenko

Beilstein J. Org. Chem. 2014, 10, 2513–2520, doi:10.3762/bjoc.10.262

• aminolysis of epoxides 6a,b afforded mainly C1 adducts 13a,b arising from trans-diaxal opening of the epoxide ring. Using a Lewis acid catalyst, epoxides 6a,b were transformed into diaminocyclopentanols 14a,b via an alternative pathway involving the formation of aziridinium intermediate 17. Keywords

• : diaminocyclopentanols; epoxides; regioselectivity; ring opening; stereoselectivity; Introduction In recent years mimicry of aminoglycosides [1][2][3][4][5][6][7] and nucleosides [8][9][10] has become an important field in pharmaceutical research. Regio- and stereochemical diversities within a sugar-like moiety in

• attack at the C1-oxirane carbon atom [29]. Synthesis of diaminocyclopentanols using epoxide 3b Next, we explored the influence of the N,N-dibenzylamino group on the ring opening reaction using the optimized reaction conditions for 3b (Table 2). Surprisingly, the ring opening of N,N-dibenzyl derivative 4b