2-Methoxy-l-naphthyl isocyanate

The cyclic carbamate (oxazolidin-2-one) 313 is formed by the reaction of phenyl isocyanate (312) with vinyloxirane[192]. Nitrogen serves as a nucleophile and attacks the carbon vicinal to the oxygen exclusively. The thermodynamically less stable Z-isomer 315 was obtained as a major product (10 1) by the reaction of 2-methoxy-l-naphthyl isocyanate (314) with a vinyloxir-... 

If 2-methoxy-l-naphthyl isocyanate is used, the N-aryloxazolidinone can be cleaved by CAN to furnish the corresponding N-unsubstituted oxazolidinone in 70-85% yield. 

To a yellow solution of the catalyst prepared by simply stirring 25.0 mg (0.12 mmol) of triisopropyl phosphite with 10.4mg (0.01 mmol) of Pd,(dba)3 CHC13 in 0.5-1.OmL of THF are added 2l9mg (1.1 mmol) of 2-methoxy-l-naphthyl isocyanate. 1 mmol of the epoxide 17a-g is added in one portion, either neat or dissolved in 1 mL of THF, and the resultant mixture is stirred at r.t. for 12—24 h until conversion is complete. Evaporation of the solvent in vacuo and flash chromatography affords the pure 2-oxazolidinones 18 a-g in the yields given in Table 7. 

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