Stereoselective synthesis of tricyclic compounds by intramolecular palladium-catalyzed addition of aryl iodides to carbonyl groups.
TL;DR: Four X-ray crystal structure analyses unequivocally defined the structure of crucial cyclization products and the formed hydroxy group in the newly generated cyclohexane ring is consistently in trans-arrangement with respect to the methoxycarbonyl group.
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Abstract: Starting from γ-ketoesters with an o-iodobenzyl group we studied a palladium-catalyzed cyclization process that stereoselectively led to bi- and tricyclic compounds in moderate to excellent yields. Four X-ray crystal structure analyses unequivocally defined the structure of crucial cyclization products. The relative configuration of the precursor compounds is essentially transferred to that of the products and the formed hydroxy group in the newly generated cyclohexane ring is consistently in trans-arrangement with respect to the methoxycarbonyl group. A transition-state model is proposed to explain the observed stereochemical outcome. This palladium-catalyzed Barbier-type reaction requires a reduction of palladium(II) back to palladium(0) which is apparently achieved by the present triethylamine.
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Citations
Nickel-Catalyzed Intermolecular Asymmetric Addition of Aryl Iodides across Aldehydes.
TL;DR: In this article , it was shown that chiral nickel complexes can catalyze the intermolecular enantioselective addition of aryl iodides across aldehydes to provide diverse optically active secondary alcohols using zinc metal as the reducing agent.
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Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)-C(sp3) bond cleavage.
TL;DR: In this article, an efficient and convenient synthesis of highly functionalized dihydropyrans was achieved through rhodium(I)-catalysed tandem C(sp3)-C(sp 3) bond cleavage and annulation of oxetanols with alkynes.
Nickel‐Catalyzed Intermolecular Asymmetric Addition of Aryl Iodides across Aldehydes
TL;DR: In this article , it was shown that chiral nickel complexes can catalyze the intermolecular enantioselective addition of aryl iodides across aldehydes to provide diverse optically active secondary alcohols using zinc metal as the reducing agent.
9
Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)–C(sp3) bond cleavage
Rui Guo,Xin-mei Zheng,Dayong Zhang,Guozhu Zhang +3 more
TL;DR: Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes affords a concise route to functionalized dihydropyrans.
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Controlling Selectivities in Palladium-Catalyzed Cyclization Reactions Leading to Heterocycles: From Ambiphilic Reactions of Arylpalladium Species to Carbene Insertions
Daniel Solé,Israel Fernández +1 more
- 01 Jan 2018
TL;DR: In this article, an overview of the work on the control of the potential ambiphilic nature of σ-organopalladium intermediates in intramolecular reactions with carbonyl derivatives is presented.
6
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