101844-21-7Relevant articles and documents
Tandem Base-Promoted Ring-Opening/Brook Rearrangement/Allylic Alkylation of O-Silyl Cyanohydrins of β-Silyl-α,β-epoxyaldehyde: Scope and Mechanism
Sasaki, Michiko,Kawanishi, Eiji,Nakai, Yoshio,Matsumoto, Tatsuya,Yamaguchi, Kentaro,Takeda, Kei
, p. 9330 - 9339 (2003)
Metalated O-silyl cyanohydrins of β-silyl-α,β -epoxyaldehyde have been found to serve as functionalized homoenolate equivalents by a tandem sequence involving base-promoted ring opening of the epoxide, Brook rearrangement, and alkylation of the resulting
Hydrosilylation of alkynes catalyzed by ruthenium carbene complexes
Maifeld, Sarah V.,Tran, Michael N.,Lee, Daesung
, p. 105 - 108 (2005)
Hydrosilylation of terminal alkynes with a variety of silanes catalyzed by Cl2(PCy3)2RuCHPh (1) affords mainly the Z-isomer via trans addition in excellent yields. The presence of a hydroxyl group in close proximity to the
Stereospecific Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Tosylate and Allyl Alcohol Electrophiles
Alexanian, Erik J.,Tercenio, Quentin D.
supporting information, p. 7215 - 7219 (2021/09/22)
The stereospecific cross-coupling of easily accessed electrophiles holds significant promise in the construction of C-C bonds. Herein, we report a nickel-catalyzed reductive coupling of allyl alcohols with chiral, nonracemic alkyl tosylates. This cross-coupling delivers valuable allylation products with high levels of stereospecificity across a range of substrates. The catalytic system consists of a simple nickel salt in conjunction with a commercially available reductant and importantly represents a rare example of a cross-coupling involving the C-O bonds of two electrophiles.
Si-directed regiocontrol in asymmetric Pd-catalyzed allylic alkylations using C1-ammonium enolate nucleophiles
Fyfe, James W.B.,Kabia, Omaru M.,Pearson, Colin M.,Snaddon, Thomas N.
, p. 5383 - 5391 (2018/04/23)
Cooperative catalysis enables the direct enantioselective α-allylation of linear prochiral esters using Si-substituted allyl electrophiles. The Si-substituent directs the regioselectivity of enantioselective bond formation and provides products containing synthetically versatile pentafluorophenyl ester and vinylsilane moieties. Critical to the efficacy of this process was the recognition that the ancillary ligand on palladium could be altered to prevent formation of a deleterious ether by-product, whilst retaining enantioselectivity through the Lewis base catalyst. Flexibility such as this is unique to cooperative catalysis events and provides efficient access to an array of enantioenriched products that are orthogonally functionalized and easily modified.
Platinum catalysed hydrosilylation of propargylic alcohols
McAdam, Catherine A.,McLaughlin, Mark G.,Johnston, Adam J. S.,Chen, Jun,Walter, Magnus W.,Cook, Matthew J.
, p. 4488 - 4502 (2013/08/23)
A facile and user-friendly protocol has been developed for the selective synthesis of E-vinyl silanes derived from propargylic alcohols using a PtCl 2/XPhos catalyst system. The reaction is generally high yielding and provides a single regioiso
