60741-75-5Relevant academic research and scientific papers
Kinetic resolution of chiral cyclohex-2-enones by rhodium(I)/binap- catalyzed 1,2- and 1,4-additions
Kolb, Andreas,Hirner, Sebastian,Harms, Klaus,Zezschwitz, Paultheo Von
supporting information; experimental part, p. 1978 - 1981 (2012/06/18)
The feasibility of kinetic resolutions of racemic monosubstituted cyclohex-2-enones by Rh/binap-catalyzed reactions was investigated. 1,2-Addition of AlMe3 to the 5-substituted derivatives furnished allylic alcohols in the matched case, while t
Annulation Based on 6-Endo-Trig Radical Cyclization: Regioselectivity and Diastereoselectivity
Ward, Dale E.,Gai, Yuanzhu,Kaller, Brian F.
, p. 7830 - 7836 (2007/10/03)
The development of a annulation strategy based on sequential "two-electron" and "one-electron" allylation of β-substituted aldehydes and derivatives with the bifunctional isobutene conjunctive reagent 1 is described.The key step involves an unusual 6-endo-trig radical cyclization.Yields of 6-endo products are improved if the PhS group is oxidized to a PhSO2 group prior to cyclization.The structural factors affecting the regioselectivity and stereoselectivity of the cyclization are examined.In general, the stereoselectivity of 6-endo-trig cyclization of 5-hexenyl radicals can be rationalized by conformational analysis of chairlike transition states and can be calculated effectively with an MM2 force field model.High 6-endo regioselectivity requires a strong driving force.Fragmentable allylic groups (R3Sn, PhSO2, and to a lesser extent PhS) are shown to be sufficiently activating to achieve 6-endo regioselectivity.
Mercurinium ion mediated ring expansion of 1-alkenyl-1-cycloalkanols
Kim,Uh
, p. 4325 - 4328 (2007/10/02)
TMS ethers of 1-alkenyl-1-cycloalkanols readily rearranged to the ring expanded β-mercurio cycloalkanones via mercurinium ions, which could be converted into α-methylene cycloalkanones through elimination and further one carbon expanded cycloalkanones via
