22422-21-5Relevant articles and documents
I2-Promoted Intramolecular Oxidative Cyclization of Butenyl Anilines: A Facile Route to Benzo[b]azepines
An, Zhenyu,Ren, Yi,Liu, Yafeng,Yan, Rulong
supporting information, p. 2614 - 2617 (2021/08/06)
A metal-free approach for the synthesis of seven-membered N-heterocycles has been developed by the I2-promoted intramolecular cross-coupling/annulation of butenyl anilines. This cyclization reaction involves C?H activation and C?C bond formation and exhibits good functional group tolerance. A series of benzo[b]azepine derivatives are obtained in moderate to good yields.
Asymmetric Hydrogenation of β-Secondary Amino Ketones Catalyzed by a Ruthenocenyl Phosphino-oxazoline-ruthenium Complex (RuPHOX-Ru): The Synthesis of γ-Secondary Amino Alcohols
Wang, Jianxia,Wang, Yanzhao,Liu, Delong,Zhang, Wanbin
supporting information, p. 3262 - 3272 (2015/11/03)
A ruthenocenyl phosphino-oxazoline-ruthenium complex (RuPHOX-Ru) was applied successfully to the asymmetric hydrogenation of β-secondary amino ketones, directly affording the corresponding chiral γ-secondary amino alcohols in up to 99% yield and with 99% ee. Reaction with β-(benzylamino)-1-phenylpropan-1-one could be performed on a gram-scale with a relatively low catalyst loading (up to 2000 S/C). The resulting hydrogenated product could be used for the synthesis of synthetically useful compounds.
Copper(II)-catalyzed hydrosilylation of ketones using chiral dipyridylphosphane ligands: Highly enantioselective synthesis of valuable alcohols
Yu, Feng,Zhou, Ji-Ning,Zhang, Xi-Chang,Sui, Yao-Zong,Wu, Fei-Fei,Xie, Lin-Jie,S. C. Chan, Albert,Wu, Jing
supporting information; experimental part, p. 14234 - 14240 (2012/01/12)
In the presence of PhSiH3 as the reductant, the combination of enantiomeric dipyridylphosphane ligands and Cu(OAc)2·H 2O, which is an easy-to-handle and inexpensive copper salt, led to a remarkably practical and versatile chiral catalyst system. The stereoselective formation of a selection of synthetically interesting β-, γ- or δ-halo alcohols bearing high degrees of enantiopurity (up to 99.9 % enantiomeric excess (ee)) was realized with a substrate-to-ligand molar ratio (S/L) of up to 10 000. The present protocol also allowed the hydrosilylation of a diverse spectrum of alkyl aryl ketones with excellent enantioselectivities (up to 98 % ee) and exceedingly high turn-over rates (up to 50 000 S/L molar ratio in 50 min reaction time) in air, under very mild conditions, which offers great opportunities for the preparation of various physiologically active targets. The synthetic utility of the chiral products obtained was highlighted by the efficient conversion of optically enriched β-halo alcohols into the corresponding styrene oxide, β-amino alcohol, and β-azido alcohol, respectively.
