4009-55-6Relevant academic research and scientific papers
Intramolecular Photocycloaddition of 4-Substituted Cyclopent-2-en-1-ones
Dauben, William G.,Rocco, Vincent P.,Shapiro, Gideon
, p. 3155 - 3160 (1985)
The intramolecular photocycloaddition of 4-(3,4-pentadienyl)cyclopent-2-en-1-ones has been shown to yield the expected straight cycloaddition product, a tricyclo4,9>nonanone, and a novel product, a tricyclo4,10>decenone, with a bridgehead double bond.The reaction course can be controlled by side-chain substituents and by the temperature of the reaction.
Rhodium-Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans
Breit, Bernhard,Schmidt, Johannes P.
supporting information, p. 23485 - 23490 (2020/10/29)
A comprehensive study of a diastereoselective Rh-catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn-selective access to synthetically important 2,4-disubstituted and 2,4,6-trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional-group compatibility and the enantioselective total synthesis of (?)-centrolobine.
Palladium-Catalyzed Stereoselective Cyclization of in Situ Formed Allenyl Hemiacetals: Synthesis of Rosuvastatin and Pitavastatin
Spreider, Pierre A.,Breit, Bernhard
supporting information, p. 3286 - 3290 (2018/06/11)
A diastereoselective palladium-catalyzed cyclization of allenyl hemiacetals is described. It permits the selective synthesis of 1,3-dioxane derivatives, precursors for syn-configured 1,3-diols which make an appearance in all of the statin representatives. The reaction allows the total synthesis of Rosuvastatin and Pitavastatin in a straightforward fashion.
Rhodium-Catalyzed Diastereoselective Cyclization of Allenyl-Sulfonylcarbamates: A Stereodivergent Approach to 1,3-Aminoalcohol Derivatives
Spreider, Pierre A.,Haydl, Alexander M.,Heinrich, Marc,Breit, Bernhard
supporting information, p. 15569 - 15573 (2016/12/09)
A diastereoselective and stereodivergent rhodium-catalyzed intramolecular coupling of sulfonylcarbamates with terminal allenes is described and it provides selective access to 1,3-aminoalcohol derivatives, scaffolds found in bioactive compounds. The reaction is compatible with a large range of different functional groups, thus furnishing products with high diastereoselectivities and yields. Moreover, multigram scale reactions, as well as the application of suitable product transformations were demonstrated.
Atom-Economical Dimerization Strategy by the Rhodium-Catalyzed Addition of Carboxylic Acids to Allenes: Protecting-Group-Free Synthesis of Clavosolide A and Late-Stage Modification
Haydl, Alexander M.,Breit, Bernhard
supporting information, p. 15530 - 15534 (2016/01/26)
Natural products of polyketide origin with a high level of symmetry, in particular C2-symmetric diolides as a special macrolactone-based product class, often possess a broad spectrum of biological activity. An efficient route to this important
Synthesis and reactions of 1,2-disubstituted methylenecyclopropanes prepared via intramolecular cyclopropanation of allenic diazoacetates
Lautens, Mark,Meyer, Christophe,Van Oeveren, Arjan
, p. 3833 - 3836 (2007/10/03)
Diazoacetates derived from α- or β-allenic alcohols, prepared using the glyoxylic acid chloride p-toluenesulfonylhydrazone method, undergo regioselective intramolecular cyclopropanation in the presence of a copper (II) catalyst in refluxing toluene, leading to synthetically useful di- or trisubstituted methylenecyclopropyl lactones. The diastereoselectivity of the process has been studied.
