128084-24-2Relevant academic research and scientific papers
Stereospecific synthesis of tetrasubstituted Z-enol silyl ethers by a three component coupling process
Corey,Lin, Shouzhong,Luo, Guanglin
, p. 5771 - 5774 (1997)
The coupling of an acylsilane, 2-propenyllithium and an alkyl halide produces tetrasubstituted Z-enol silyl ether in good yields, and provides the first route to these isomerically pure compounds.
Enantioconvergent Cross-Couplings of Alkyl Electrophiles: The Catalytic Asymmetric Synthesis of Organosilanes
Schwarzwalder, Gregg M.,Matier, Carson D.,Fu, Gregory C.
supporting information, p. 3571 - 3574 (2019/02/13)
Metal-catalyzed enantioconvergent cross-coupling reactions of alkyl electrophiles are emerging as a powerful tool in asymmetric synthesis. To date, high enantioselectivity has been limited to couplings of electrophiles that bear a directing group or a pro
Enantio-, Regio- and Chemoselective Copper-Catalyzed 1,2-Hydroborylation of Acylsilanes
Nagy, Audric,Collard, Laurent,Indukuri, Kiran,Leyssens, Tom,Riant, Olivier
supporting information, p. 8705 - 8708 (2019/06/13)
Enantioselective synthesis of synthetically significant (α-hydroxyallyl)silanes, (α-hydroxyaryl)silanes, and (α-hydroxyalkyl)silanes is reported. The present copper-catalyzed 1,2-selective hydroborylation of acylsilanes affords the aforementioned products
Intermolecular Schmidt reaction of alkyl azides with acyl silanes
Yu, Chun-Jiao,Li, Rui,Gu, Peiming
supporting information, p. 3568 - 3570 (2016/07/18)
The first intermolecular Schmidt reaction of alkyl azides with acyl silanes has been designed and realized, producing a range of amides with absolute site selectivity in good to excellent yields. The mechanism of the conversion has been proposed, and the reaction exhibits scope of substrates.
Acylsilane chemistry. Synthesis of regio- and stereoisomerically defined enol silyl ethers using acylsilanes
Reich, Hans J.,Holtan, Ronald C.,Bolm, Carsten
, p. 5609 - 5617 (2007/10/02)
The preparation of enol silyl ethers using a carbonyl addition-Brook rearrangement-elimination sequence was studied. The key intermediate α-silyl-β-X-alkoxides could be prepared in several different ways, including the addition of organolithium or hydride reagents to α-X-acylsilanes (path a, using RM with R = alkyl, aryl, vinyl, alkynyl, silyl, stannyl, phosphinyl, and cyano), the addition of α-X-lithium reagents to acylsilanes (path b, X = phenylthio, phenylsulfonyl), or the addition of silyllithium reagents to α-X-ketones (path c, X = phenylthio, alkoxy). All of the reactions gave complete regiocontrol of silyl enol ether formation, and many gave excellent (>99%) stereocontrol as well. The selectivity of the carbonyl addition, silyl rearrangement, and elimination was studied. For path a, when the R group of RM was a poor carbanion stabilizing group the elimination of the intermediate α-silyl-β-X-alkoxides was stereospecific, and there was a large difference in rate between erythro and threo (erythro > threo). When R was a carbanion stabilizing group, such as aryl or alkynyl, the elimination process became nonstereospecific in some cases, and only small differences between threo and erythro were observed. Path b was especially effective with α-sulfonyl lithium reagents, and these reactions gave predominantly E enol silyl ethers (4/1 to 20/1). The addition of organolithium reagents to β-X-acylsilanes (the homologue of path a) was also briefly explored as a synthesis of siloxy-cyclopropanes.
