Skip to main content
. Author manuscript; available in PMC: 2016 Mar 17.
Published in final edited form as: ACS Comb Sci. 2012 Apr 2;14(4):285–293. doi: 10.1021/co300003c

Table 3.

Regio- and Stereoselective Spirocyclization to Afford 2- and 3-spirooxazoline Scaffolds

graphic file with name nihms368205t3.jpg

entry R isatin oxazole product yield (%)a drb
1 5-F 3b 11e 17b 55c 90:10
2 4-Cl 3c 11e 17c 74 99:1
3 H 3a 11f 18a 77c 90:10
4 5-F 3b 11f 18b 87 93:7
5 4-Cl 3c 11f 18c 51c 95:5
6 5-Br 3d 11f 18d 95 99:1
a

Isolated yield of major diastereomer.

b

Determined by analysis of 1H NMR spectroscopy of crude reaction mixture.

c

Yields sacrificed for purity due to the presence of by-products which proved to be difficult to separate by column chromatography (conversion ≥80% by TLC).