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Expedient Syntheses of β‐Iodofurans by 5‐ endo ‐ dig Cyclisations
Author(s) -
Bew Sean P.,
ElTaeb Gamila M. M.,
Jones Simon,
Knight David W.,
Tan WenFei
Publication year - 2007
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.200700681
Subject(s) - chemistry , electrophile , regioselectivity , dig , halogen , alkyne , hydroxylation , organic chemistry , conjugated system , transition metal , combinatorial chemistry , total synthesis , catalysis , alkyl , polymer , computer security , computer science , enzyme
5‐ endo ‐ dig cyclisations of 3‐alkyne‐1,2‐diols using iodine as the electrophile proceed smoothly to deliver excellent yields of the corresponding β‐iodofurans. The necessary precursors are available from a number of different approaches, notably regioselective bis‐hydroxylation of conjugated enynes and the addition of acetylides to α‐hydroxy carbonyl groups. The initial iodofurans can be homologated using a number of strategies, ranging from various transition metal‐catalysed couplings to halogen–metal exchange and subsequent coupling with an electrophile. Hence, this method overall represents a flexible, relatively brief and very efficient approach to a variety of highly substituted furans. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)