89414-11-9Relevant academic research and scientific papers
Intramolecular [2+2] photocycloaddition-fragmentation: Facile entry to a novel tricyclic 5-6-7 ring system
Hong, Bor-Cherng,Chen, Shang-Hung,Kumar, Ellappan Sampath,Lee, Gene-Hsiang,Lin, Kuan-Jiuh
, p. 917 - 926 (2007/10/03)
An expeditious route to a novel 5-6-7 tricyclic ring system is described. The chemistry capitalizes on an enantioselective glyoxylate-ene reaction, enzymatic resolution as well as a [2+2] photocycloaddition-fragmentation.
Total Synthesis of (+/-)-Nitramine. Development of a Ketene Equivalent in the Ene Reaction
Snider, Barry B.,Cartaya-Marin, Claudia P.
, p. 1688 - 1691 (2007/10/02)
(+/-)-Nitramine (1a) was synthesized in seven steps from methylenecyclohexane in 33percent overall yield.A three-step sequence was developed from methylenecyclohexane to aldehyde 4 in which methyl α-chloroacrylate was used as a ketene equivalent in the ene reaction.Aldehyde 4 was converted to nitrone 3 which cyclized to a 2.5:1 mixture of 2 and 9.Hydrogenolysis of 2 gave 1a.Lewis acid catalyzed cyclization of 4 gave a 3.5:1 mixture of hydrindanones 13 and 14 at 25 deg C and a 12:1 mixture of 13 and 14 at -20 deg C.
