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.
Denmark
Scott E
SE
Department of Chemistry, Roger Adams Laboratory, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Xie
Min
M
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