345218-02-2Relevant academic research and scientific papers
Copper-catalyzed enantioselective hydroboration of unactivated 1, 1-disubstituted alkenes
Jang, Won Jun,Song, Seung Min,Moon, Jong Hun,Lee, Jin Yong,Yun, Jaesook
supporting information, p. 13660 - 13663 (2017/11/07)
We report an efficient and highly enantioselective hydroboration of aliphatic 1, 1-disubstituted alkenes with pinacolborane using a phosphine-Cu catalyst. The method allows facile preparation of enantiomerically enriched β-chiral alkyl pinacolboronates from a range of 1, 1-disubstituted alkenes with high enantioselectivity up to 99% ee. Unprecedented enantiodiscrimination between the geminal alkyl substituents was observed with functional group compatibility in the hydroboration. Furthermore, a catalyst loading as low as 1 mol % furnished the desired product without a decrease in yield or selectivity, demonstrating its efficiency in gram scale synthesis.
The highly enantioselective transformation of silylketenes into α-silylthioesters catalysed by cinchona alkaloids
Blake, Alexander J.,Friend, Christopher L.,Outram, Robert J.,Simpkins, Nigel S.,Whitehead, Andrew J.
, p. 2877 - 2881 (2007/10/03)
The reaction of silylketenes with thiophenol, mediated by cinchona alkaloid catalysts, proceeds to give α-silylthioester products in good chemical yield and with enantiomeric excess values in the range 79-93%. The absolute configuration of one of the thioester products was determined by X-ray diffraction.
