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. 2014 Oct 28;10:2513–2520. doi: 10.3762/bjoc.10.262

Table 3.

Epoxide ring opening of 3a–d containing different substituents on the nitrogen atom.

graphic file with name Beilstein_J_Org_Chem-10-2513-i003.jpg
Entry Epoxide R1 R2 Reaction time, ha Product (C1)b Product (C2)b rr (C1:C2)
1 3a Me Bn 2 8a – >19:1
2 3b Bn Bn 2 9a 10a 2:1
3 3c Ph Bn 6 11 12 5:1c
4 3d Ph Ph 6d – – –

aReagents and conditions: 5.0 mmol epoxide, 10.0 mol % Zn(ClO4)2·6H2O, 6.5 mmol morpholine (7a), neat, 100 °C. bProducts formed due to the nucleophilic attack at the C1 or C2 oxirane carbon atoms. cThe regiochemistry was established from 1H NMR analysis of the mixture. dNo reaction was observed.