4 research outputs found

    Amino Acid Salts Catalyzed Asymmetric Aldol Reaction of Tryptanthrin: A Straightforward Synthesis of Phaitanthrin A and Its Derivatives

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    The first asymmetric synthesis of (<i>S</i>)-Phaitanthrin A and its derivatives via a catalytic aldol reaction of Tryptanthrin and ketones is described, in which the cheap, easily prepared natural amino acid salts exhibited unique catalytic ability; importantly, this methodology tolerates a range of substrates with different substitution patterns. Moreover, the synthetic utility of this strategy was further illustrated by a gram-scale synthesis of Phaitanthrin A

    Direct Catalytic Asymmetric Synthesis of β‑Hydroxy Acids from Malonic Acid

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    A nickel­(II) catalyzed asymmetric synthesis of β-hydroxy acids from malonic acid and ketones was developed, revealing for the first time the synthetic utility of malonic acid in the construction of chiral carboxyl acids; importantly, the synthetic potential of this strategy was further demonstrated by the rapid construction of cephalanthrin A, phaitanthrin B, cruciferane, and rice metabolites

    Rhodium(III)-Catalyzed Oxidative Annulation of 2,2′-Bipyridine N‑Oxides with Alkynes via Dual C–H Bond Activation

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    Rh­(III)-catalyzed switchable annulation of 2,2′-bipyridine N-oxides with internal alkynes via dual C–H bond activation has been developed. Tuning the reaction conditions enabled the reaction pathway to be switched between rollover and nonrollover annulation, delivering 5,6-disubstituted-1,10-phenanthrolines and 5,6,7,8-tetrasubstituted-1-(pyridin-2-yl)­isoquinoline 2-oxides in high yields, respectively. The procedures feature excellent regioselectivity, broad substrate scope, and high tolerance of functional groups. The synthetic utilities of these obtained products were demonstrated in the catalytic reactions
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