Highly diastereoselective samarium diiodide induced cyclizations of new 3-substituted indole derivatives.
Herein, we describe the synthesis of new functionalized tricyclic and tetracyclic indole derivatives via samarium diiodide induced ketyl cyclizations. The intermediate samarium organyls were either protonated using different proton sources or alkylated with various electrophiles in a highly diastereoselective manner. The obtained products were subjected to further transformations leading to synthetically interesting building blocks.
Beemelmanns
Christine
C
Hans-Ulrich Reissig, Institut für Chemie und Biochemie, Takustr. 3, 14195, Berlin, Germany.
Reissig
Hans-Ulrich
HU
D000097:Acetonitriles / Q000737:chemistry; D000470:Alkaloids; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000097:Acetonitriles; D000470:Alkaloids; D007211:Indoles; D007454:Iodides; D007659:Ketones; D012493:Samarium; C409809:samarium diiodide; C032159:acetonitrile