Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: synthesis of 3-substituted azepanes.
A novel gamma-selective conjugate addition of 1-silyl-substituted dienol ethers to nitroalkenes activated by Lewis acids has been developed. The resulting alpha,beta-unsaturated acylsilanes undergo photoinduced protodesilylation to afford the corresponding enals, which can be conveniently transformed into azepanes under appropriate reductive conditions.
Department of Chemistry, Roger Adams Laboratory, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Scott E
SE
Denmark
Min
M
Xie
D000143:Acids / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D001381:Azepines / Q000138:chemical synthesis / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*
D000143:Acids; D000475:Alkenes; D001381:Azepines; D004987:Ethers; D009574:Nitro Compounds; D012821:Silanes