[2+3] CycloadditionsBetween Nitroalkenes and Camphor-Derived OxazolineN-Oxidesand Radical Denitration of the Adducts

Abstract

2+3] Cycloadditions between camphor-derived oxazoline N-oxide 2 and nitroalkenes 3a-f afforded stereoselectively adducts 4a-f. Radical denitration followed by acidic hydrolysis gave rise to anti-aldols 8a,b. The radical intermediate was also trapped by a suitable alkene, giving rise to a single stereoisomer.

The Last Fortress of Tin's Tyranny – Protodenitration of Nitroalkanes

“…Figure 7. Application of the Ono-Tanner reaction between 1999 and 2007 byBallini (1999),[139] Grossman (1999),[140] Guo and Fuchs (1999),[141] Danishefsky (2000),[142] Danishefsky (2001),[143] Martin (2000),[144] Trost (2000),[145] Uno (2000),[146] Román and Light (2001),[147] Hu (2001),[148] Le Gall and Mioskowski (2001),[149] Crich (2002),[150] Gurjar (2002),[151] Crich (2003),[152] Estévez (2003),[153] Kouklovksy and Langlois (2003),[154] Loghmani-Khouzani (2004),[155] Barret (2005),[156] Kitazume (2005),[157] Crich (2006),[158] Jahn (2006),[159] Luzzio (2006),[160] Petrini (2006)[161] and Alajarín and López-Leonardo (2007) [162]. *Other major products were formed.…”