TY - JOUR
T1 - Expedient syntheses of β-iodofurans by 5-endo-dig cyclisations
AU - Bew, Sean P.
AU - El-Taeb, Gamila M. M.
AU - Jones, Simon
AU - Knight, David W.
AU - Tan, Wen-Fei
PY - 2007/12
Y1 - 2007/12
N2 - 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, 2007.
AB - 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, 2007.
UR - http://www.scopus.com/inward/record.url?scp=36849044131&partnerID=8YFLogxK
U2 - 10.1002/ejoc.200700681
DO - 10.1002/ejoc.200700681
M3 - Article
VL - 2007
SP - 5759
EP - 5770
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 34
ER -