A nickel-catalyzed reductive coupling between acid fluorides and vinyl triflates has been described. This method provides an efficient access to various enones and avoids the requirement for acyl or vinyl metallic reagents in the conventional approaches. The reaction proceeds with a broad range of acid fluorides and cyclic vinyl triflates, tolerating several functional groups. The utility of this synthetic method has been demonstrated by the late-stage modification of pharmaceuticals and biologically active natural compounds.
Because of the importance of the indole framework and the versatile transformation of nitro and formyl groups, the efficient synthesis of optically pure 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanals, one type of tryptamine precursors are of great interest for pharmaceutical and biological research. Herein, the Michael addition of aliphatic aldehydes to indolylnitroalkenes has been developed using (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst, which provides the desired optically pure syn 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanal derivatives in up to 98% yield with up to >99:1 dr and >99% ee. To show the synthetic usefulness of this methodology, optically active 2-alkyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butan-1-ol and tryptamine derivatives are readily obtained by stepwise systematic transformations.
Optically active hydrobenzoins are very important building blocks for further derivation of biologically active complexes, natural products, and pharmaceutical compounds. In this paper, A practical approach has been developed for asymmetric hydrogenation of benzils with Ru(OTf)(TsDPEN)(η6‐cymene) as a pre‐catalyst in methanol. Therefore, a series of chiral hydrobenzoins was synthesized in good yields with good to moderate diastereoselectivities and good to excellent enantioselectivities.
Given the importance of indane derivatives in both organic and medicinal chemistry, the development of an effective synthetic protocol for the preparation of multifunctionalized 1,2,3‐trisubstituted indane derivatives is of considerable interest. In this paper, we developed a cascade regio‐ and enantioselective double Michael addition to construct challenging multifunctionalized chiral indane derivatives in the presence of a bifunctional acid–base organocatalyst. The resulting optically active indane derivatives with three alternating trans stereocenters were produced in moderate to good yields with excellent diastereoselectivities and excellent enantioselectivities. Remarkably, the resulting products were facilely converted into multifunctionalized optically active (1‐indanylmethyl)amine and tetrahydroindeno[2,1‐b]pyrrole derivatives.
Dibenzyls are essential building blocks widely used in organic synthesis, and they are typically prepared by the homocoupling of halides, organometallics, and ethers. Herein, we reported an approach to this class of compounds using alcohols, which are more stable and readily available. The reaction proceeds via nickel-catalyzed and DMO-assisted dynamic kinetic homocoupling of benzyl alcohols. Both primary and secondary alcohols are tolerated.
Construction of 3-Amino-2-oxindoles by Direct Amination of Aniline or-Amino-Acid Derivatives to 3-Bromooxindoles. -The Ni-catalyzed asymmetric amination of 3-bromooxindoles with anilines is developed. In the presence of a bisoxazolidine catalyst moderate ee's are obtained. Moreover, the uncatalyzed reaction with amino acid esters gives low diastereoselectivities. -(ZHAO, M.; LI, N.-K.; ZHANG, Y.
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