226387-12-8Relevant articles and documents
Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents
Farley, Conner M.,Zhou, You-Yun,Banka, Nishit,Uyeda, Christopher
supporting information, p. 12710 - 12714 (2018/10/09)
Cyclic structures are highly represented in organic molecules, motivating a wealth of catalytic methods targeting their synthesis. Among the various ring-forming processes, cyclooligomerization reactions possess several attractive features but require addressing a unique challenge associated with controlling ring-size selectivity. Here we describe the catalytic reductive cocyclooligomerization of an enone and three carbene equivalents to generate a cyclopentane, a process that constitutes a formal [2 + 1 + 1 + 1]-cycloaddition. The reaction is promoted by a (quinox)Ni catalyst and uses CH2Cl2/Zn as the C1 component. Mechanistic studies are consistent with a metallacycle-based pathway, featuring sequential migratory insertions of multiple carbene equivalents to yield cycloalkanes larger than cyclopropanes.
Pd(II)/tBu-quinolineoxazoline: An Air-Stable and modular chiral catalyst system for enantioselective oxidative cascade cyclization
He, Wei,Yip, Kai-Tai,Zhu, Nian-Yong,Yang, Dan
supporting information; experimental part, p. 5626 - 5628 (2010/03/02)
[Chemical Equation Presented] An air-stable and structurally tunable chiral tBu-quinolineoxazoline/Pd(II) catalyst system has been developed for the enantioselective oxidative cascade cyclization of a variety of disubstituted olefinic substrates, with the apparent advantages of good yields and excellent enantioselectivities (up to 98% ee) and diastereoselectivities (dr >24:1). A transition-state model has also been proposed to account for the excellent stereocontrol.
Steric effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation using chiral oxazolinylpyridines
Chelucci, Giorgio,Medici, Serenella,Saba, Antonio
, p. 543 - 550 (2007/10/03)
Eight new chiral oxazolinylpyridines were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3- diphenylprop-2-enyl acetate with dimethyl malonate. Catalytic activity and enantioselectivity were found to be highly