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. Author manuscript; available in PMC: 2009 Sep 14.
Published in final edited form as: Org Lett. 2008 Jun 14;10(14):2951–2954. doi: 10.1021/ol8009072

Table 1.

Synthesis of Seven- and Eight-Membered Ring Sultams via Intramolecular Oxa-Michael Reactions

graphic file with name nihms-116098-t0007.jpg
entry product n R1 R2 total yielda (%)
1 4a 1 i-Pr CH2CH=CH2 61
2 4b 1 CH2Ph CH2Ph(o-Br) 60
3 4c 2 H CH2CH=CH2 54
4 4d 1 CH2Ph CH2Ph(o-Me) 59b
5 4e 2 H CH2Ph(o-F) 53b
6 4f 1 i-Bu CH2Ph(m-Cl) 58b
7 4g 1 i-Bu CH2Ph 61b
a

Total yield of all four steps.

b

Sultams 4d—g were synthesized through chromatography-free linear synthesis; see Supporting Information for reaction procedure.