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Highly Selective Synthetic Method for 1,6‐Diols Bearing Enyne Functions: Development of 3,6‐Dianion Reagent of 1,2‐Hexadien‐4‐yne Using 1,6‐Dibromo‐2,4‐hexadiyne and Indium
Author(s) -
Kim Sundae,
Lee Kooyeon,
Seomoon Dong,
Lee Phil Ho
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700309
Subject(s) - chemistry , chemoselectivity , reagent , regioselectivity , tetrahydrofuran , enyne , lithium iodide , lithium (medication) , indium , iodide , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , medicine , electrode , solvent , electrolyte , endocrinology
The reaction of aldehydes and ketones with an organoindium reagent generated in situ from indium and 1,6‐dibromo‐2,4‐hexadiyne in the presence of lithium iodide in tetrahydrofuran (THF) selectively produced 1,6‐diols linked to an allenyne unit with complete regioselectivity and chemoselectivity through 1,2‐hexadien‐4‐yn‐3,6‐ylation, indicating that the organoindium acted as the 3,6‐dianion reagent of 1,2‐hexadien‐4‐yne.