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. Author manuscript; available in PMC: 2008 Aug 26.
Published in final edited form as: Chem Rev. 2007 May 27;107(6):2503–2545. doi: 10.1021/cr0509556

Table 5.

Kinetic resolution of racemic terminal epoxides with Me3SiN3 catalyzed by (R,R)-(salen)CrN3 under solvent-free conditions.

graphic file with name nihms-63649-t0022.jpg
entry R cat. mol% yield (%)b ee (%) krel
1 CH3 1.0 98 97 230
2 CH2CH3 2.0 83 97 140
3 (CH2)3CH3 2.0 89 97 160
4 CH2OTBDMS 3.0 96 96 150
5 CH2O(1-naphthyl) 5.0 74 93 48
6 CH2C6H5 2.0 94 93 71
7 c-C6H11 2.0 84c 97 140
8 (CH2)2CH=CH2 2.0 94 98 280
9 CH(OEt)2 2.0 96 89 44
10 CH2CN 2.0 80 92 45
a

Reactions were run without solvent for 18-50 h at 0-2 °C.

b

Isolated yield of the azido sily ether based on TMSN3.

c

Isolated yield of the azido alcohol.