5205-34-5Relevant articles and documents
Copper-Catalyzed Reductive Ireland-Claisen Rearrangements of Propargylic Acrylates and Allylic Allenoates
Guo, Siyuan,Wong, Kong Ching,Scheeff, Stephan,He, Zhuo,Chan, Wesley Ting Kwok,Low, Kam-Hung,Chiu, Pauline
, p. 429 - 452 (2022/01/03)
The copper-catalyzed reductive Ireland-Claisen rearrangement of propargylic acrylates led to 3,4-allenoic acids. The use of silanes or pinacolborane as stoichiometric reducing agents and triethylphosphite as a ligand facilitated the divergent and complementary selectivity for the synthesis of diastereomeric anti- and syn-rearranged products, respectively. Copper-catalyzed reductive Ireland-Claisen rearrangement of allylic 2,3-allenoates proceeded effectively only when pinacolborane was used as a reductant to generate various 1,5-dienes in excellent yields and with good diastereoselectivities in some cases. Mechanistic studies showed that the silyl and boron enolates, rather than the copper enolate, underwent a stereospecific rearrangement via a chairlike transition state to afford the corresponding Claisen rearrangement products.
Copper-catalyzed aerobic oxidative functionalization of C-H bonds of alkanes in the presence of acetaldehyde under mild conditions
Hayashi, Yukiko,Komiya, Naruyoshi,Suzuki, Ken,Murahashi, Shun-Ichi
, p. 2706 - 2709 (2013/06/26)
Copper-catalyzed oxidative functionalization of C-H bonds of alkanes with molecular oxygen has been performed in the presence of Cu(OAc)2 catalyst and acetaldehyde in acetonitrile at 70 C with extremely high turn-over numbers.
Regio- And stereoselective subterminal hydroxylations of n-decane by fungi in a liquid-liquid interface bioreactor (L-L IBR)
Oda, Shinobu,Isshiki, Kunio,Ohashi, Shinichi
experimental part, p. 105 - 109 (2009/04/10)
This article may be the first report to describe the excellent regio- and stereoselective subterminal hydroxylations of n-alkane with microorganisms. Approximately 2000 fungal strains were screened for the regioselective hydroxylation of n-decane with a s