TY - JOUR A1 - Schmidt, Bernd A1 - Staude, Lucia A1 - Kelling, Alexandra A1 - Schilde, Uwe T1 - A Cross-Metathesis-Conjugate addition route to enantiopure gamma-Butyrolactams and gamma-Lactones from a C-2-Symmetric Precursor JF - European journal of organic chemistry N2 - A protected derivative of (3R, 4R)-hexa-1,5-diene-3,4-diol, a conveniently accessible C-2-symmetric building block, undergoes single or double cross metathesis with methyl acryl-ate. The cross metathesis products are amenable to stereoselective conjugate addition reactions and can be converted into either gamma-butyrolactones or gamma-lactams. KW - Lactams KW - Lactones KW - Oxygen heterocycles KW - Metathesis KW - Desymmetrization Y1 - 2011 U6 - https://doi.org/10.1002/ejoc.201001528 SN - 1434-193X IS - 9 SP - 1721 EP - 1727 PB - Wiley-Blackwell CY - Malden ER - TY - JOUR A1 - Schmidt, Bernd A1 - Krehl, Stefan T1 - A single precatalyst tandem RCM-allylic oxidation sequence JF - Chemical communications N2 - Ring closing metathesis of allyloxy styrenes and a subsequent Ru-catalyzed allylic oxidation can be combined to a tandem sequence that makes coumarins accessible using less active but more conveniently available first generation catalysts. Y1 - 2011 U6 - https://doi.org/10.1039/c1cc11347j SN - 1359-7345 VL - 47 IS - 20 SP - 5879 EP - 5881 PB - Royal Society of Chemistry CY - Cambridge ER - TY - JOUR A1 - Schmidt, Bernd A1 - Hölter, Frank T1 - Suzuki-Miyaura cross coupling reactions with Phenoldiazonium salts JF - Organic & biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry N2 - The Suzuki-Miyaura coupling of phenol diazonium salts and aryl trifluoroborates yields 4-hydroxybiaryls in a protecting group-free synthesis. Y1 - 2011 U6 - https://doi.org/10.1039/c1ob05256j SN - 1477-0520 VL - 9 IS - 13 SP - 4914 EP - 4920 PB - Royal Society of Chemistry CY - Cambridge ER - TY - JOUR A1 - Schmidt, Bernd A1 - Geissler, Diana T1 - Olefin-Metathesis-Based Synthesis of Furans by an RCM/Deprotonation/Phosphorylation Sequence and Their Diels-Alder Reactions JF - European journal of organic chemistry N2 - Butenolides, obtained by ring-closing metathesis (RCM) of acrylates, undergo quantitative deprotonation with amide bases. Trapping of the resulting anions with electrophiles, for example, chlorophosphates, give furans. Subsequent DielsAlder reaction and acid-catalysed rearrangement of the resulting oxabicyclonorbornadienes give substituted benzenes. KW - Lactones KW - Metathesis KW - Ruthenium KW - Oxygen heterocycles KW - Metalation Y1 - 2011 U6 - https://doi.org/10.1002/ejoc.201101078 SN - 1434-193X IS - 35 SP - 7140 EP - 7147 PB - Wiley-VCH CY - Weinheim ER - TY - JOUR A1 - Schmidt, Bernd A1 - Geissler, Diana T1 - Ru- and Pd-Catalysed Synthesis of 2-Arylfurans by One-Flask Heck Arylation/Oxidation JF - European journal of organic chemistry N2 - 2,5-Disubstituted furans were synthesized by one-flask Heck arylation/oxidation sequences. The starting materials are 2-substituted 2,3-dihydrofurans, conveniently available by RCM/isomerization sequences, and arenediazonium salts. These react in ligand-free Heck reactions to afford 2,5-disub-stituted 2,5-dihydrofurans, which are oxidized to the corresponding furans without isolation or intermediate workup. The oxidation is conveniently achieved with chloranil or DDQ, depending on the substrate. KW - Diazonium salts KW - Palladium KW - C-C coupling KW - Heck coupling KW - Furans KW - Oxidation KW - Oxygen heterocycles Y1 - 2011 U6 - https://doi.org/10.1002/ejoc.201100549 SN - 1434-193X IS - 25 SP - 4814 EP - 4822 PB - Wiley-VCH CY - Weinheim ER - TY - JOUR A1 - Schmidt, Bernd A1 - Berger, René A1 - Kelling, Alexandra A1 - Schilde, Uwe T1 - Pd-Catalyzed [2+2+1] coupling of alkynes and arenes phenol diazonium salts as mechanistic trapdoors JF - Chemistry - a European journal N2 - Alkynes and phenol diazonium salts undergo a Pd-catalyzed [2+2+1] cyclization reaction to spiro[4,5]decatetraene-7-ones. This structure was confirmed for one example by X-ray single-crystal structure analysis. The reaction is believed to proceed through oxidative addition of the phenol diazonium cation to Pd(0), subsequent insertion of two alkynes, followed by irreversible spirocyclization. KW - alkynes KW - diazo compounds KW - palladium KW - phenols KW - spirocycles Y1 - 2011 U6 - https://doi.org/10.1002/chem.201100609 SN - 0947-6539 VL - 17 IS - 25 SP - 7032 EP - 7040 PB - Wiley-Blackwell CY - Malden ER - TY - JOUR A1 - Reznichenko, Alexander L. A1 - Emge, Thomas J. A1 - Audoersch, Stephan A1 - Klauber, Eric G. A1 - Hultzsch, Kai C. A1 - Schmidt, Bernd T1 - Group 5 metal binaphtholate complexes for catalytic asymmetric hydroaminoalkylation and hydroamination/cyclization JF - Organometallics N2 - 3,3'-Silylated binaphtholate tantalum and niobium complexes were shown to be efficient catalysts for the asymmetric hydroaminoalkylation of N-methylaniline derivatives and N-benzylmethylamine with simple alkenes in enantioselectivities of up to 80% ee. No hydroaminoalkylation was observed with aminoalkenes; rather, exclusive asymmetric hydroamination/cyclization took place in up to 81% ee. Y1 - 2011 U6 - https://doi.org/10.1021/om1011006 SN - 0276-7333 VL - 30 IS - 5 SP - 921 EP - 924 PB - American Chemical Society CY - Washington ER -