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Efficient Synthesis of Medium‐Sized Rings Incorporating Indole or Pyrrole Units by Samarium Diiodide Induced Cyclizations
Author(s) -
Blot Virginie,
Reißig HansUlrich
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600743
Subject(s) - chemistry , samarium , intramolecular force , stereocenter , indole test , pyrrole , moiety , stereochemistry , samarium diiodide , alkylation , medicinal chemistry , enantioselective synthesis , organic chemistry , catalysis
Samarium diiodide promoted the intramolecular reductive couplings of N ‐alkylated indole and pyrrole derivatives 9 – 12 and 14 to afford products 15 – 19 that incorporate seven‐ and eight‐membered rings. They were obtained in good yields and generally with excellent diastereoselectivities. Up to four contiguous stereogenic centres are controlled in this transformation, which is explained by a highly ordered transition structure with the samarium alcoholate moiety preferring an equatorial position. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)