Reaction of α,α′-dibromo ketones with iron carbonyls in the presence of five-membered heterocycles

Metal-Assisted Cycloaddition Reactions in Organotransition Metal Chemistry

“…Schemes 24 and 25). 415,416,420,[657][658][659][660][661][662][663][664][665] in particular have strongly contributed to the development of the methodology. The use of Fe 2 (CO) 9 to reductively dehalogenate the R,R′-dibromo ketones has the advantage that through coordination to iron, a great variety of oxyallyl cations 180 (cf.…”

Electronic Donation or Steric Contraction: A Spectroscopic and Structural Analysis of Medium-Sized Constrained Rings for Potential Long-Range Hyperconjugation

“…The collected organic matter was dried in vacuo to yield crude 3 . The product was purified via flash chromatography in silica gel (3:1 hexane/EtOAc, rf 0.45) to yield 91.0 mg (7.66% yield) of 3 as a solid, confirmed by comparison with literature data outlined by Noyori …”

“…The product was purified via flash chromatography in silica gel (3:1 hexane/EtOAc, rf 0.45) to yield 91.0 mg (7.66% yield) of 3 as a solid, confirmed by comparison with literature data outlined by Noyori. 25 Ethyl (1R,2R,5S,6S)-10-Oxo-11-azatricyclo[4.3.1.12,5]undec-3ene-11-carboxylate (5). General Procedure.…”

New chemical and stereochemical applications of organoiron complexes

“…For instance, 212 underwent [3 + 4] cycloaddition with open-chain dienes, producing substituted 4-cycloheptenones [ 401 ]. In addition, the cycloaddition of cyclic dienes including cyclopentadiene [ 401 , 402 ], and heteroaromatics such as pyrroles [ 401 , 403 ] and furans [ 401 , 404 ], gives bridged ketone systems. The reaction with furans proceeds by a concerted process, with the regioselectivity controlled by the frontier molecular orbitals of the two reactants [ 405 ].…”