443988-55-4Relevant academic research and scientific papers
Highly Efficient Access to Both Geometric Isomers of Silyl Enol Ethers: Sequential 1,2-Brook/Wittig Reactions
Matsuya, Yuji,Wada, Kentaro,Minato, Daishiro,Sugimoto, Kenji
, p. 10079 - 10082 (2016)
Novel sequential 1,2-Brook/Wittig reactions were developed for the preparation of silyl enol ethers. This method enables highly selective preparation of both geometric isomers of glyoxylate silyl enol ethers, using aldehydes (E-selective) and tosylimines
Organocatalyzed Direct Aldol Reaction of Silyl Glyoxylates for the Synthesis of α-Hydroxysilanes
Han, Man-Yi,Xie, Xiaoyu,Zhou, Di,Li, Pinhua,Wang, Lei
supporting information, p. 2282 - 2285 (2017/05/12)
A novel organocatalyzed direct aldol reaction of aldehydes to silyl glyoxylates is disclosed. This method provides an efficient route to α-hydroxysilanes with excellent enantioselectivities (up to 99% ee) and high diastereoselectivities (up to >20:1 dr). In the new activation model of silyl glyoxylates, the hydrogen bond is critical to the reaction. A carbonyl group directly attached to silicon in acylsilanes could be activated by coordination to the proton of hydroxyl and carboxylic acid via a hydrogen bond. Moreover, commercially available cis-l-4-hydroxyproline is an ideal organocatalyst for activating both aldehydes and acylsilanes.
Synthesis and use of α-silyl-substituted α-hydroxyacetic acids
Bolm, Carsten,Kasyan, Andrey,Heider, Peter,Saladin, Sandra,Drauz, Karlheinz,Guenther, Kurt,Wagner, Christoph
, p. 2265 - 2267 (2007/10/03)
(matrix presented) Rhodium-catalyzed oxygen transfer was used to generate benzyl 2-silyl-2-oxoacetates in good yields. The hydrogenation of these compounds led to chiral α-silyl-substituted α-hydroxyacetic acids. Resolution by means of HPLC using a chiral stationary phase afforded an enantiomerically pure representative of this class of compounds, which was successfully applied as a chiral ligand in an asymmetric aldol-type reaction.
