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Regioselective Addition of Allylindium Reagents to Allenes in Functionalized 1,6‐Diols Bearing Allenynes
Author(s) -
Kim Sundae,
Ho Lee Phil
Publication year - 2008
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.200800027
Subject(s) - chemistry , regioselectivity , markovnikov's rule , reagent , lithium (medication) , lithium iodide , halide , iodide , organic chemistry , butyllithium , methyl iodide , indium , free radical addition , medicinal chemistry , combinatorial chemistry , catalysis , medicine , electrode , electrolyte , endocrinology
Addition reactions of allylindium reagents generated in situ from indium and allyl halides to functionalized allenyne 1,6‐diols proceeded regioselectively through anti‐Markovnikov addition to produce exclusively dienyne 1,6‐diols in good yields in THF at 70 °C. In the case of 3‐bromo‐2‐methylpropene, lithium iodide was used as an additive. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)