66374-47-8Relevant academic research and scientific papers
Synthese regioselective par voie organometallique de vinylsilanes fonctionnels a partir de derives carbonyles α-ethyleniques α-trimethylsilyles
Mesnard,Hanai,Miginiac
, p. 125 - 135 (2007/10/03)
The α-trimethylsilyl conjugated carbonyl derivatives 1 easily react with organometallics 2 (M = Al, Mg, Zn) and allow preparation of functional vinylsilanes 3 or 4, in regioselective manner: R'-CH C(SiMe3)-C(OH)(R')(R) 3; (R')(R)CH-C(SiMe3)C(R')(OSiMe3) 4.
Highly Regio- and Diastereoselective One-Pot Synthesis of Silyl Epoxy Alcohols and Vinylsilanes by Direct Hydroxy-Epoxidation
Adam, Waldemar,Richter, Markus J.
, p. 3341 - 3346 (2007/10/02)
A direct synthesis of silyl epoxy alcohols from vinylsilanes is described.It consists of the regioselective ene reaction of the vinylsilanes with singlet oxygen, which proceeds with predominant hydrogen abstraction at the position geminal to the silyl group.The resulting silyl allylic hydroperoxides were treated, without isolation, subsequently with Ti(O-i-Pr)4 to afford the silyl epoxy alcohols in good yields and very high diastereomeric ratios, which ranged from 93:7 to greater than 97:3.Alternatively, the vinylsilanes were photooxygenated directly in the presence of the titanium catalyst and the silyl epoxy alcohols obtained in good yields.The method was applied to di- and trisubstituted acyclic vinylsilanes with a methyl group geminal to silicon and cyclic derivatives all give consistently good results.In this novel hydroxy-epoxidation, the regioselectivity of the singlet oxygen ene reaction as well as the diastereoselectivity of the oxygen transfer can be controlled by the steering effects of the silyl group.
The synthesis of 3-trimethylsilyl-4-dimethyl(phenyl)silyl-but-3-en-2-one, a β-functionalised Michael acceptor
Fleming,Newton,Sabin,Zammattio
, p. 7793 - 7802 (2007/10/02)
The title compound 3 has been prepared by silyl-cupration of trimethylsilylacetylene followed by acetylation. The phenyldimethylsilyl group can be removed selectively in a three-step procedure to give 3-trimethylsilylbut-3-ene-2-one 1b. The enone 3 and cyclohexanone can be used in an annelation reaction to make 5-dimethyl(phenyl)silylbicyclo[4.4.0]decan-3-one 20 and hence to make 2-vinylcyclohexylacetic acid 23.
Studies directed towards the selective C-2 opening of 2,3-epoxy alcohols with azide ion
Chakrabory,Reddy
, p. 679 - 682 (2007/10/02)
The generally observed preference for C-3 opening of simple 2,3-epoxyalcohols was reversed when a silyl group was introduced at 2-position.
ALTERNATIVE SYNTHESES AND DIELS-ALDER REACTIONS OF 2,3-Bis(TRIMETHYLSILYL)BUTA-1,3-DIENE
Garratt, Peter J.,Tsotinis, Andrew
, p. 2761 - 2762 (2007/10/02)
The title compound has been prepared by two routes and some Diels-Alder reactions of it investigated.
Tandem Pd-Catalyzed Elimination-Cyclization
Trost, Barry M.,Mignani, Serge
, p. 3435 - 3439 (2007/10/02)
Attempted generation of 2-(trimethylsilyl)buta-1,3-diene by palladium-catalyzed elimination of 3-acetoxy-2-(trimethylsilyl)-1,3-butadiene led instead to 3-(trimethylsilyl)-1,3,7-octatriene, a potentially useful building block.Such a product presumably ari
A REGIOSPECIFIC SYNTHESIS OF TRIMETHYLSILYL ENOL ETHERS USING RHODIUM CATALYZED ISOMERIZATION OF β-TRIMETHYLSILYLALLYL ALCOHOLS
Matsuda, Isamu,Sato, Susumu,Izumi, Yusuke
, p. 2787 - 2790 (2007/10/02)
The rhodium catalyzed isomerization of β-trimethylsilylallyl alcohols has been successfully applied for the regiospecific synthesis of trimethylsilyl enol ethers.
SILICON IN ORGANIC SYNTHESIS-17 CYCLOPENTANNULATION BY THERMOLYSIS OF (1-TRIMETHYLSILYLCYCLOPROPYL)ETHYLENES-THE 1-TRIMETHYLSILYLCYCLOPROPYL ANION
Paquette, Leo A.,Wells, Gregory J.,Horn, Keith A.,Yan, Tu-Hsin
, p. 913 - 924 (2007/10/02)
Several alternatives for preparing (1-trimethylsilylcyclopropyl)ethylenes have been examined.Although 1-lithio-1-(trimethylsilyl)ethylene does add satisfactorily to carbonyl compounds and the subsequent Simmons-Smith cyclopropanation provides the desired
A CONVENIENT SYNTHETIC METHOD FOR 3-TRIMETHYLSILYLBUTENONE
Okumoto, Hiroshi,Tsuji, Jiro
, p. 1015 - 1020 (2007/10/02)
Convenient synthetic method for 2-trimethylsilylbutenone from acrolein is presented.
