Samarium Diiodide Induced Cyclization Reactions
Publications
| • | A. J. Achazi*, D. Andrae, H.-U. Reißig, B. Paulus A Computational Study of Samarium Diiodide-Induced Cyclizatons of N-Oxoalkyl-Substituted Methyl Indole-3-Carboxylates - A Rationale of the Diastereoselectivity J. Comput. Chem. 2017, 38, 2693 – 2700. |
| • | C. N. Rao, C. Bentz, H.-U. Reissig* Lithium Bromide/Water as Additives in Dearomatizing Samarium-Ketyl (Hetero)Arene Cyclizations Chem. Eur. J. 2015, 21, 15951 – 15954. |
| • | C. Beemelmanns, H.-U. Reissig* Strychnine as Target, Samarium Diiodide as Tool: A Personal Story Chem. Rec. 2015, 15, 872 – 885. |
| • | C. Beemelmanns, H.-U. Reißig* Evolution of a Short Route to Strychnine by Using the Samarium-Diiodide-Induced Cascade Cyclization as a Key Step Chem. Eur. J. 2015, 21, 8416 – 8425. |
| • | C. N. Rao, D. Lentz, H.-U. Reißig* Synthese polycyclischer tertiärer Carbinamine durch Samariumdiiodid-vermittelte Cyclisierungen von Indolylsulfinylimien Angew. Chem. 2015, 127, 2788 – 2792. C. N. Rao, D. Lentz, H.-U. Reißig* Synthesis of Polycyclic Tertiary Carbinamines by Samarium Diiodide Mediated Cyclizations of Indolyl Sulfinyl Imines Angew. Chem. Int. Ed. 2015, 54, 2750 – 2753. |
| • | M. Kandziora, H.-U. Reißig* Synthesis of Rigid p-Terphenyl-Linked Carbohydrate Mimetics Beilstein J. Org. Chem. 2014, 10, 1749 – 1758. |
| • | C. Beemelmanns, S. Gross, H.-U. Reißig* Towards the Core Structure of Strychnos Alkaloids Using Samarium Diiodide-Induced Reactions of Indole Derivatives Chem. Eur. J. 2013,19, 17801 – 17808. |
| • | A. Niermann, J. E. Grössel, H.-U. Reißig* New Thiochromans via Reductive Cyclization of Thiophenol Derivatives Synlett 2013, 177 – 180. |
| • | M. Jasiński,T. Watanabe, H.-U. Reißig* Samarium Diiodide Promoted Reduction of 3,6-Dihydro-2H-1,2-oxazines: Competition of 1,4-Amino Alcohol Formation and Ring Contraction to Pyrrole Derivatives Eur. J. Org. Chem. 2013, 605 – 610. |
| • | M. Berndt, A. Hölemann, A. Niermann, C. Bentz, R. Zimmer, H.-U. Reißig* Replacement of HMPA in Samarium Diiodide Promoted Cyclizations and Reactions of Organolithium Compounds Eur. J. Org. Chem. 2012, 1299 – 1302. |
| • | C. Beemelmanns, D. Lentz, H.-U. Reißig* Samarium Diiodide Induced Cyclizations of γ-, δ- and ε-Indolyl Ketones: Reductive Coupling, Intermolecular Trapping, and Subsequent Transformations of Indolines Chem. Eur. J. 2011, 17, 9720 – 9730. |
| • | C. Beemelmanns, H.-U. Reißig* Samarium diiodide induced ketyl-(het)arene cyclisations towards novel N-heterocycles Chem. Soc. Rev. 2011, 40, 2199 – 2210. |
| • | A. Niermann, H.-U. Reißig* Influence of Geminal Disubstitution on Samarium Diiodide Induced Reductive Cyclizatons of γ-Aryl Ketones Synlett 2011, 525 – 528. |
| • | C. Beemelmanns, H.-U. Reißig* New Samarium Diiodide-Induced Cyclizations Pure Appl. Chem. 2011, 83, 507 – 517. |
| • | J. Saadi, I. Brüdgam, H.-U. Reißig* Highly Substituted Benzannulated Cyclooctanol Derivatives by Samarium Diiodide-Induced Cyclizations Beilstein Journal of Organic Chemistry 2010, 6, No. 141, (1229 – 1245). |
| • | C. Beemelmanns, H.-U. Reißig* Eine kurze formale Strychnin-Totalsynthese mit einer Samariumdiiodid-induzierten Kaskadenreaktion als Schlüsselschritt Angew. Chem. 2010, 122, 8195 – 8199. C. Beemelmanns, H.-U. Reißig* A Short Formal Total Synthesis of Strychnine with a Samarium Diiodide Induced Cascade Reaction as the Key Step Angew. Chem. Int. Ed. 2010, 49, 8021 – 8025. |
| • | U. K. Wefelscheid, H.-U. Reißig* Synthesis of New Steroid Analogues by Samarium Diiodide Induced Cyclisations of γ-Naphthyl 1,3-Diones Tetrahedron: Asymmetry 2010, 21, 1601 – 1610. |
| • | C. Beemelmanns, V. Blot, S. Gross, D. Lentz, H.-U. Reißig* Highly Diastereoselective Samarium Diiodide Induced Ketyl Cyclisations of Indole and Pyrrole Derivatives – Scope and Limitations Eur. J. Org. Chem. 2010, 2716 – 2732. |
| • | C. Beemelmanns, H.-U. Reißig* Highly diastereoselective samarium diiodide induced cyclizations of new 3-substituted indole derivatives Org. Biomol. Chem. 2009, 7, 4475 - 4480. |
| • | J. Saadi, H.-U. Reißig* Scope and Limitations of Samarium Diiodide Induced Cyclizations of Alkenyl-Substituted γ-Keto Esters to Benzannulated Cyclooctanol Derivatives Synlett 2009, 2089 - 2092. |
| • | J. Saadi, D. Lentz, H.-U. Reißig* Medium-Sized Carbocycles by Samarium Diiodide-Induced Carbonyl-Alkene Cyclizations Org. Lett. 2009, 11, 3334 - 3337. |
| • | U. K. Wefelscheid, M. Berndt, H.-U. Reißig* Samarium Diiodide Mediated Ketyl-Aryl Couplings – Influence of Substituents and Trapping Experiments Eur. J. Org. Chem. 2008, 3635– 3646. |
| • | R. S. Kumaran, I. Brüdgam, H.-U. Reißig* Modular and Stereoselective Synthesis of Hydroxylated Angularly Fused Tricyclic Piperidine Derivatives via Samarium Diiodide-Mediated Cyclization Synlett, 2008, 991 – 994. |
| • | F. Aulenta, U. K. Wefelscheid, I. Brüdgam, H.-U. Reißig* Nitrogen-Containing Tricyclic and Tetracyclic Compounds via Stereoselective Samarium Diiodide Promoted Cyclizations of Quinolyl-Substituted Ketones – A New Access to Azasteroids Eur. J. Org. Chem. 2008, 2325 - 2335. |
| • | U. K. Wefelscheid, H.-U. Reißig* Pentacyclic Compounds by Samarium Diiodide-Induced Cascade Cyclizations of Naphthyl-Substituted 1,3-Diones Adv. Synth. Catal, 2008, 350, 65 – 69. |
| • | U. K. Wefelscheid, I. Brüdgam, H. Hartl, H.-U. Reißig* Crystal structure of (8S*,9S*,13S*,14R*,17S*)-estra-1(10),2,4,6-tetraene- 14,17-diol monohydrate, C18H22O2 H2O Z. Kristallogr. NCS 2007, 222, 467 – 468. |
| • | U. K. Wefelscheid, I. Brüdgam, H.-U. Reißig* Crystal structure of (8S*,9S*,13R*,14R*,17S*)-9,17-cycloestra-1(10), 2,4,6-tetraene-14,17-diol trihydrate, C18H20O23H2O Z. Kristallogr. NCS 2007, 222, 465 – 466. |
| • | F. Aulenta, M. Berndt, I. Brüdgam, H. Hartl, S. Sörgel, H.-U. Reißig* A New, Efficient and Stereoselective Synthesis of Tricyclic and Tetracyclic Compounds by Samarium Diiodide Induced Cyclisations of Naphthyl-Substituted Arylketones – An Easy Access to Steroid-Like Skeletons Chem. Eur. J. 2007, 13, 6047 – 6062. |
| • | V. Blot, H.-U. Reißig* Efficient Synthesis of Medium-Sized Rings Incorporating Indole or Pyrrole Units by Samarium Diiodide Induced Cyclizations Eur. J. Org. Chem. 2006, 4989 - 4992. |
| • | F. Aulenta, H.-U. Reißig Heck Reactions of Quinoline-Derived Nonaflates Synlett 2006, 2993 – 2996. |
| • | V. Blot, H.-U. Reißig* Highly Substituted Dihydroindole Derivatives by Intermolecular Couplings of Samarium Ketyls and Indoles Synlett 2006, 2763 - 2766. |
| • | H.-U. Reißig*, F. A. Khan, R. Czerwonka, C. U. Dinesh, A. L. Shaikh, R. Zimmer Benzannulated Cyclooctanol Derivatives by Samarium Diiodide Induced Intramolecular Carbonyl-Alkene Coupling - Scope, Limitations, Stereoselectivity Eur. J. Org. Chem. 2006, 4419 - 4428. |
| • | F. Aulenta, A. Hölemann, H.-U. Reißig* Samarium Diiodide Induced Reactions of Cyclopropyl Ketones: Reductive Ring Cleavage and Dimerization Leading to 1,8-Diketones - Scope, Limitations, Mechanism Eur. J. Org. Chem. 2006, 1733 - 1739. |
| • | A. Hölemann, H.-U. Reißig* Samarium Diiodide in the Synthesis of Medium-Sized Rings - Carbocycles and Heterocycles by Intramolecular Addition of Samarium Ketyls to Alkynes Synlett 2004, 2732 - 2735. |
| • | A. Hölemann, H.-U. Reißig* Regioselective Samarium Diiodide-Induced Couplings of Carbonyl Compounds with 1,3-Diphenylallene and Alkoxyallenes - A New Route to 4-Hydroxy 1-Enol Ethers Chem. Eur. J. 2004, 10, 5493 - 5506. |
| • | A. Hölemann, H.-U. Reißig* Synthesis of New Furan Derivatives and 4-Hydroxy Aldehydes from 4-Hydroxy 1-Enol Ethers Synthesis 2004, 1963 – 1970. |
| • | M. Berndt, I. Hlobilová, H.-U. Reißig* Stereoselective Formation of Tri- and Tetracycles by Samarium Diiodide- Induced Cyclizations of Naphthyl-Substituted Ketones Org. Lett. 2004, 6, 957 - 960. |
| • | A. Hölemann, I. Brüdgam, H. Hartl*, H.-U. Reißig Crystal Structure of cis-(5E)-Phenylmethylidenedecahydro-4aH-benzo[a]cyclo- hepten-4a-ol, C18H24O Z. Kristallogr. NCS 2004, 219, 59 - 60. |
| • | S. Groß, I. Brüdgam, H. Hartl*, H.-U. Reißig Crystal Structure of (9aRS,10SR,10aRS)-8-Methoxy-10-methyl- 1,2,3,5,7,9a,10,10a-octahydropyrrolo[1,2-b]isoquinoline-10-ol, C14H21NO2 Z. Kristallogr. NCS 2004, 219, 57 - 58. |
| • | S. Groß, I. Brüdgam, H. Hartl*, H.-U. Reißig Crystal Structure of (4SR,4aSR)-1-Acetyl-4-hydroxy-4,8-dimethyl-1,2,3,4,4a,7- hexahydroquinoline, C13H19NO2 Z. Kristallogr. NCS 2004, 219, 55 - 56. |
| • | S. Groß, I. Brüdgam, H. Hartl*, H.-U. Reißig Crystal Structure of (2RS,4SR,4aSR)-1-Acetyl-2-(1-methylethyl)-4-hydroxy- 4-methyl-1,2,3,4,4a,7-hexahydroquinoline, C15H22NO2 Z. Kristallogr. NCS 2004, 219, 53 - 54. |
| • | M. Berndt, I. Brüdgam, H. Hartl*, H.-U. Reißig Crystal Structure of 1-Isopropyl-15-oxatetracyclo[11.2.1.02,11.05,10]hexadeca- 3,5(10),6,8-tetraen-14-one, C18H20O2 Z. Kristallogr. NCS 2004, 219, 51 - 52. |
| • | M. Berndt, I. Brüdgam, H. Hartl*, H.-U. Reißig Crystal Structure of (1aSR,5bRS,7aSR,10aRS,10bSR,10cRS)-1a,5b,6,7,7a,8,9,10, 10b,10c-Decahydro-10aH-cyclopenta[1,2]phenanthro[9,10-b] oxiren-10a-ol, C17H20O2 Z. Kristallogr. NCS 2004, 219, 49 - 50. |
| • | M. Berndt, I. Brüdgam, H. Hartl*, H.-U. Reißig Crystal Structure of (2SR,1'RS)-3-(1-Naphthyl)-2-(2-oxocyclopentyl)-propionic acid methyl ester, C19H20O3 Z. Kristallogr. NCS 2004, 219, 47 - 48.
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| • | M. Berndt, S. Groß, A. Hölemann, H.-U. Reißig* New Samarium Diiodide-Induced Ketyl Couplings – From Analogous Reactions to Serendipitously Discovered Processes Synlett 2004, 422 – 438. |
| • | S. Groß, H.-U. Reißig* Novel Stereoselective Syntheses of Highly Functionalized Benzannulated Pyrrolizidines and Indolizidines by Samarium Diiodide-Induced Cyclizations of Indole Derivatives Org. Lett. 2003, 5, 4305 - 4307. |
| • | A. Hölemann, H.-U. Reißig* Samarium Diiodide-Induced Couplings of Carbonyl Compounds with Methoxyallene Leading to 4-Hydroxy 1-Enol Ethers Org. Lett. 2003, 5, 1463 - 1466.
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| • | S. Groß, H.-U. Reißig* Samarium Diiodide-Induced Diastereoselective Synthesis of Hexahydroquinoline Derivatives Synlett 2002, 2027 - 2030. |
| • | O. Rademacher*, R. Zimmer, C. U. Dinesh, H. U. Reißig Crystal structure of 2SR,5SR,5aSR,11bSR-5-Methyl-1,5,5a,11b- tetrahydro-2,5-methanonaphtho[2,1-c]oxepin-3(2H)-one, C16H16O2 Z. Kristallogr. NCS 2002, 217, 425 - 426. |
| • | O. Rademacher*, R. Zimmer, C. U. Dinesh, H. U. Reißig Crystal structure of Methyl 4aSR,5RS,12aRS-12a-Hydroxy- 1,2-3,4,4a,5,6,11,12,12a-decahydro-dibenzo[a,e][8]annulene-5-carboxylate, C18H24O3 Z. Kristallogr. NCS 2002, 217, 423 - 424.
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| • | O. Rademacher*, M. Berndt, H.-U. Reißig Crystal Structure of 4R*,4aS*,5S*-5-Hydroxy-4-(1-hydroxy-1-methylethyl)-5- methyl-4,4a,5,6,7,8-hexahydronaphthalene-2-carbonitrile—water (1/1), C15H21NO2 H2O. Kristallogr. NCS 2001, 216, 593 – 594. |
| • | D. Lentz*, E. Nandanan, H.-U. Reißig Crystal Structure of 6S*,8S*-9-Butyl-8-hydroxy-8-isopropyl-5,6,7,8-tetra hydrobenzocyclooctene-6-carboxylate, C21H30NO3 Z. Kristallogr. NCS 2001, 216, 525 – 526. |
| • | Berndt, H.-U. Reißig* Substituent Effects in Samarium Diiodide-Induced 6-trig Cyclizations of γ-Aryl ketones to Functionalized Hexahydronaphthalene Derivatives Synlett 2001, 1290 – 1292. |
| • | C. U. Dinesh, H.-U. Reißig, O. Rademacher* Crystal structure of methyl 4aR*,4bR*,8aS*,9R*-1-cyano-4b-hydroxy-2,4a, 4b,5,6,7,8,8a,9, 10-decahydro- phenanthrene-9-carboxylate, C17H21NO3 Z. Kristallogr. NCS 2000, 215, 615 - 616. |
| • | E. Nandanan, C. U. Dinesh, H.-U. Reißig* Competition between Novel 8-endo-dig and 6-trig Cyclizations of Samarium Ketyls Leading either to Benzannulated Cyclooctene or to Hexahydronaphthalene Derivatives Tetrahedron 2000, 56, 4267 - 4277. |
| • | R. Zimmer, G. Zahn*, F. A. Khan, H.-U. Reißig* Configurational Analysis of 14,14-Dimethyl-12-oxatricyclo[9.2.1.03,8]tetradeca- 3,5,7-trien-13-one Acta Crystallogr. Sect. C 1999, 55, 1941 - 1943. |
| • | C. U. Dinesh, H.-U. Reißig* Eine neue Samariumdiiodid-induzierte Reaktion: intramolekularer Angriff von Ketylradikalanionen auf Arylsubstituenten unter Bildung von 1,4-Cyclohexadienderivaten Angew. Chem. 1999, 111, 874 - 876. |
| C. U. Dinesh, H.-U. Reißig* A New Samarium Diiodide Induced Reaction: Intramolecular Attack of Ketyl Radical Anions on Aryl Substituents with Formation of 1,4-Cyclohexadiene Derivatives Angew. Chem. Int. Ed. 1999, 38, 789 - 791. |
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| • | F. A. Khan, R. Czerwonka, R. Zimmer, H.-U. Reißig* A Novel Sm(II)-Induced Route to Highly Substituted Benzannulated Cyclooctanol Derivatives Synlett 1997, 995 - 997. |