849996-35-6Relevant academic research and scientific papers
Anti-Markovnikov Hydrofunctionalization of Alkenes: Use of a Benzyl Group as a Traceless Redox-Active Hydrogen Donor
Lonca, Geoffroy Hervé,Ong, Derek Yiren,Tran, Thi Mai Huong,Tejo, Ciputra,Chiba, Shunsuke,Gagosz, Fabien
supporting information, p. 11440 - 11444 (2017/09/11)
A protocol for the anti-Markovnikov hydrofunctionalization of alkenes has been developed by the use of a benzyl group as a traceless redox-active hydrogen donor. Under copper catalysis and in the presence of CF3- or N3-containing hyp
Facially controlled C-methylation of oxolanyl and cyclopentyl acetate enolates: Application to the total synthesis of (+)-nephromopsinic acid
Mulzer, Johann,Steffen, Ulrich,Martin, Harry J.,Zorn, Ludwig
, p. 1028 - 1043 (2007/10/03)
The stereoselectivity of the C-methylation of oxolanyl and cyclopentyl acetate enolates 5a-22a was investigated. The configuration of the C-methyl diastereomers was elucidated by a combination of crystal structure analysis, NMR spectroscopy and chemical correlations. Generally, the methylation proceeded re*-selectively, although with very different degrees of selectivity. The most important stereodirecting effect was a steric one exerted by the 5-phenethyl substituent, and this steric effect was strongly increased by the stereodirecting effect of a 3-OR group. Contrary to previous literature evidence, the endocyclic oxolanyl oxygen does not exert an effect. These findings were applied in a highly stereoselective synthesis of (+)-nephromopsinic acid (94). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
