N-Heterocyclic Carbene as a Catalyst in Ring-Opening Reactions
SHORT COMMUNICATION
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Scheme 3. Possible mechanism for the ring-opening reactions of
aziridines with acid anhydrides catalyzed by N-heterocyclic car-
bene.
In conclusion, we have developed an efficient and conve-
nient method for the ring-opening reactions of aziridines [3]
with acid anhydrides that are catalyzed by N-heterocyclic
carbene. The nucleophilic N-heterocyclic carbene shows
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with acid anhydrides, are ongoing.
Experimental Section
General Procedure for the Reactions of Aziridines 1 with Acid Anhy-
dride: Acid anhydride (1.2 equiv.) was added to a solution of azirid-
ine 1 (0.25 mmol) and NHC A (5 mol-%) in DMF (2.0 mL). The
reaction mixture was stirred at 80 °C for a period of time indicated
in Table 1. After the reaction was complete as monitored by TLC,
the mixture was washed with saturated NH4Cl and extracted with
ethyl acetate. The organic extracts were dried (MgSO4), filtered,
and concentrated under reduced pressure. Purification by column
chromatography on silica gel afforded the corresponding product.
Selected example: trans-2-(4-methylphenylsulfonamido)cyclohexyl
acetate (2a).[11] 1H NMR (400 MHz, CDCl3): δ = 1.10–1.40 (m, 4
H), 1.61–1.71 (m, 2 H), 1.76 (s, 3 H), 1.86–1.98 (m, 1 H), 1.99–2.15
(m, 1 H), 2.42 (s, 3 H), 3.15–3.29 (m, 1 H), 4.51–4.61 (dt, J = 12.0,
4.0 Hz, 1 H), 4.86 (d, J = 8.0 Hz, 1 H), 7.28 (d, J = 8.0 Hz, 2 H),
7.74 (d, J = 8.0 Hz, 2 H) ppm.
Acknowledgments
We thank Professor Xue-Long Hou for his invaluable advice during
the course of this research. Financial support from the National
Natural Science Foundation of China (20502004) and the Science
and Technology Commission of Shanghai Municipality
(05ZR14013) is gratefully acknowledged.
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