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. Author manuscript; available in PMC: 2012 Jun 22.
Published in final edited form as: J Am Chem Soc. 2011 May 23;133(24):9216–9219. doi: 10.1021/ja202900h

Table 3.

Stereoselective synthesis of (2,3-anti-3,4-syn-4,5-anti-5,6-anti)-1-aza-7-oxabicyclo[2.2.1]heptanes.

graphic file with name nihms298691u4.jpg
entry homoallylic hydroxylamine yield (%) dr product
1 graphic file with name nihms298691t43.jpg
43 		64 ≥20:1 graphic file with name nihms298691t44.jpg
44
2 graphic file with name nihms298691t45.jpg
45 		55 ≥20:1 graphic file with name nihms298691t46.jpg
46
3 graphic file with name nihms298691t47.jpg
47 		64 ≥20:1 graphic file with name nihms298691t48.jpg
48
4 graphic file with name nihms298691t49.jpg
49 		52 ≥20:1 graphic file with name nihms298691t50.jpg
50
5 graphic file with name nihms298691t51.jpg
34 		60 ≥20:1 graphic file with name nihms298691t52.jpg
51

Note: products are racemic.