Intramolecular [4 + 2] cycloaddition of nitroalkenes for construction of vicinal quaternary stereocenters.
[chemical reaction: see text]. Nitroalkene (E)-1 has been synthesized to test the feasibility of an intramolecular [4 + 2] cycloaddition in a planned synthesis of daphnilactone B. This nitro olefin contains two unique structural features, a nitromethylene lactone and a pendant diene, that combine under the action of SnCl4 in a highly selective fashion to afford nitronates 2a and 2b. These products represent the correct relationship for the vicinal quaternary stereogenic centers in the core of daphnilactone B.
Denmark
Scott E
SE
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Baiazitov
Ramil Y
RY
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D008968:Molecular Conformation; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D009574:Nitro Compounds