- Trans-Selective and Switchable Arene Hydrogenation of Phenol Derivatives
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A trans-selective arene hydrogenation of abundant phenol derivatives catalyzed by a commercially available heterogeneous palladium catalyst is reported. The described method tolerates a variety of functional groups and provides access to a broad scope of trans-configurated cyclohexanols as potential building blocks for life sciences and beyond in a one-step procedure. The transformation is strategically important because arene hydrogenation preferentially delivers the opposite cis-isomers. The diastereoselectivity of the phenol hydrogenation can be switched to the cis-isomers by employing rhodium-based catalysts. Moreover, a protocol for the chemoselective hydrogenation of phenols to cyclohexanones was developed.
- Bergander, Klaus,Glorius, Frank,Heusler, Arne,Wollenburg, Marco
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p. 11365 - 11370
(2020/11/24)
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- Photochemical rearrangement of N -chlorolactams: A route to N -heterocycles through concerted ring contraction
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We report a novel ring contraction allowing the direct conversion of N-chlorolactams to their corresponding ring-contraction N-heterocycles upon photolysis. Results show that the rearrangement occurs with a variety of N-chlorolactams and that the greater the substitution at the migrating carbon, the greater the yield of product. Importantly, stereochemistry at the migrating carbon is conserved in the product. Rearranged products were isolated as their methyl carbamates in yields varying from 17% to 58%, with the major side product being the recyclable parent lactam.
- Winter, Dana K.,Drouin, Alexandre,Lessard, Jean,Spino, Claude
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supporting information; experimental part
p. 2610 - 2618
(2010/06/17)
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- Chemoenzymatic enantioselective synthesis of 3-hydroxy-2-pyrrolidinones and 3-hydroxy-2-piperidinones
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The enantioselective synthesis of 3-hydroxypyrrolidin-2-ones and 3-hydroxy piperidin-2-ones has been carried out in high enantiomeric excess employing immobilized lipase from Pseudomonas cepacia.
- Kamal, Ahmed,Ramana, K. Venkata,Ramana, A. Venkata,Babu, A. Hari
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p. 2587 - 2594
(2007/10/03)
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- The synthesis and chemistry of 3-diazo-piperidin-2-one
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The efficient synthesis of 3-diazo-piperidin-2-one, from L-ornithine, in two steps is reported. The chemistry of this new cyclic α-diazoamide was explored and allows the rapid access to a wide range of 3-substituted piperidin-2-one derivatives.
- Hutchinson, Ian S,Matlin, Stephen A,Mete, Antonio
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p. 3137 - 3143
(2007/10/03)
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- Synthesis and Serotonin-Receptor Activity of Substituted 1-Oxo-1,2,3,4-tetrahydro-&β-carbolines
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2,3-Dihydroxypyridine is used as a starting material for the synthesis of donor and acceptor substituted 1-oxo-1,2,3,4-tetrahydro-β-carbolines via Fisher indole cyclisation.An alkaloid from Alstonia venenata is prepared.All compounds inclusive strychnocarpine show low affinity to the serotonine receptor. - Key words: 3-Hydroxy-2-pyridone, Strychnocarpine Derivatives, 5-Hydroxytryptamine Receptor Stimulators
- Herdeis, Claus,Bissinger, Gerhard
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p. 785 - 790
(2007/10/02)
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