20680-18-6

Upstream product

• 1063994-90-0 C₂₃H₃₆B₂O₆ 
• 99902-35-9 5-phenylpent-1-yn-3-ol 
• 104-53-0 3-phenyl-propionaldehyde 
• 1026082-30-3 4-oxo-1-phenylpentan-3-yl acetate 
• 140149-77-5 5-phenyl-1-trimethylsilylpent-1-yn-3-ol 
• 100330-45-8 (+/-)-1-(2-Phenylethyl)-3-propynyl acetate 

Relevant academic research and scientific papers

Mechanism and scope of the cyanide-catalyzed cross silyl benzoin reaction

In this work, cross silyl benzoin addition reactions between acylsilanes (1) and aldehydes (2) catalyzed by metal cyanides are described. Unsymmetrical aryl-, heteroaryl-, and alkyl-substituted benzoin adducts can be generated in moderate to excellent yie

CATALYZED ENANTIOSELECTIVE TRANSFORMATION OF ALKENES

Enantioselective catalytic reactions that operate directly on unactivated alkenes for the preparation of chiral organic building blocks and new materials. More particularly, a catalyzed enantioselective reaction that operates on an unsaturated hydrocarbon, such as an alkene, to provide an enantiomerically enriched reactive organometallic intermediate, which can be converted to a variety of multifunctional optically active reaction products.

Cross silyl benzoin additions catalyzed by lanthanum tricyanide

From a screen of (cyanide)metal complexes, an improved catalyst for the cross silyl benzoin addition was discovered. Several M(CN)3 complexes (M = Ce, Er, Sm, Y, Yb, La) were evaluated and lanthanum tricyanide was identified as the optimal cata

Hydroxyl-directed intermolecular ketone-olefin couplings promoted by SmI2

SmI2-promoted intermolecular ketone-olefin couplings are facilitated and stereocontrolled by hydroxyl groups incorporated within the starting materials. For example, the SmI2-induced ketone-olefin coupling reactions of α-hydroxy ketone 5 with ethyl acrylate, acrylonitrile, ethyl crotonate, and 2(5H)-furanone proceeded with high stereocontrol to afford the syn-1,2-diol products 6-9 in good yields. Excellent diastereoselectivity was achieved in the reductive couplings of β-hydroxy aldehyde 21 and erythro-β-hydroxy ketone 24 with acrylonitrile using SmI2, to produce the anti-1,3-diols 22 and 25 in good yields. The sense of the stereoselectivity was in full accord with a chelation-control model. In the proposed model, the stereochemistry of the reaction product is explained by assuming that a cyclic ketyl radical is generated during the initial single-electron reduction by SmI2. This radical species results from the chelation of the Sm(III) cation, attached to the ketyl radical, with the hydroxyl group.

Samarium(II) Iodide Promoted Intermolecular Ketone-Olefin Couplings Chelation-Controlled by α-Hydroxyl Groups

The hydroxyl group directed intermolecular ketone-olefin coupling reactions induced by SmI2 between α-hydroxyl ketones and α,β-unsaturated esters occurred with excellent stereochemical control about the newly formed asymmetric centers.