Markovnikov Alkyne Hydrosilylation Catalyzed by Ruthenium Complexes

and, Barry M. Trost; Ball, Zachary T.

doi:10.1021/ja0121033

Cited by 286 publications

(128 citation statements)

References 16 publications

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“…The use of ruthenium complex [Cp*RuA C H T U N G T R E N N U N G (MeCN) 3 ]PF 6 and (EtO) 3 SiH for hydrosilylation of the alkynes enabled a highly chemoand stereoselective trans addition [82] in good yields and also showed good compatibility with a variety of functional groups. In the desilylation step, AgF was used as a mild fluoride source, which led to rapid, quantitative and selective desilylation under mild conditions (Scheme 21).…”

Section: Macrocyclic (E)-alkenesmentioning

confidence: 99%

Alkyne Metathesis: Catalysts and Synthetic Applications

2007

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There has been rapid progress and growing interest in alkyne metathesis within the past decade. The availability of highly active catalysts as well as their applications in both organic synthesis and polymer chemistry has served to motivate the advancement of this field. In this article, the development of several different metathesis catalysts, including two heterogeneous ones, are reviewed with an emphasis on comparing strengths and weaknesses. In Section 4, the applications of alkyne metathesis to synthesis of natural products, conjugated polymers as well as shape-persistent macrocycles are discussed. In the last section, a comparison of alkyne metathesis to the well established alkene metathesis is given. Developing an alkyne metathesis catalyst with both high reactivity and robustness to air and moisture remains an unsolved problem of this important and useful reaction.

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Section: Macrocyclic (E)-alkenesmentioning

confidence: 99%

Alkyne Metathesis: Catalysts and Synthetic Applications

2007

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“…Ruthenium-catalyzed regioselective hydrosilylation [33] transformed alkyne 22 into vinyl silane 52 in high yields and with minimal degradation in the enantiomeric ratio. Vinyl silanes have shown great utility in the formation of C − H, [43] C − C, [35] and C − O [36] bonds and provide a route to more elaborated chiral building blocks.…”

Section: Synthetic Utility: the Rapid Generation Of Chiral Building Bmentioning

confidence: 99%

Dinuclear Zinc‐Catalyzed Asymmetric Desymmetrization of Acyclic 2‐Substituted‐1,3‐Propanediols: A Powerful Entry into Chiral Building Blocks

Trost

Malhotra

Mino

et al. 2008

Chemistry A European J

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The asymmetric acylation of meso 2-substituted-1,3-propanediols using an amphoteric chiral dinuclear zinc catalyst is described. It is has been demonstrated that both 2-alkyl-and 2-aryl-1,3-propanediols can be desymmetrized in high yields and enantioselectivities using the same family of ligands. Given that both antipodes of the chiral catalyst are available, both enantiomers of the desymmetrized product can be obtained from the same starting material.The synthetic utility of the desymmetrized products has been demonstrated by the synthesis of several chiral building blocks with high enantiomeric purities.

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“…To circumvent the problem, we decided to switch the order of our synthetic sequence and performed the ruthenium-catalyzed hydrosilylation reaction prior to the RCM step. Thus, dienyne 7 was first hydrosilylated under the conditions developed by Trost and Ball [11] with HSi(OEt) 3 in the presence of [Cp*Ru(MeCN) 3 ]PF 6 (1 mol %), and subjected subsequently to RCM with the second-generation Grubbs catalyst ([Ru]-II; 5 mol %) to afford the corresponding d-lactone. The d-lactone was then treated with AgF to remove the two silyl groups (Table 2, entry 2).…”

Section: Entry 1)mentioning

confidence: 99%