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Direct Preparation of 7‐Allyl‐ and 7‐Arylindolines
Author(s) -
Leonori Daniele,
Coldham Iain
Publication year - 2009
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.200900499
Subject(s) - chemistry , transmetalation , tetramethylethylenediamine , regioselectivity , triphenylphosphine , negishi coupling , aryl , medicinal chemistry , ligand (biochemistry) , palladium , organic chemistry , zinc , combinatorial chemistry , catalysis , biochemistry , alkyl , receptor
Addition of allyl halides to the organolithium species derived from lithiation of N ‐ tert ‐butoxycarbonylindoline with sec ‐butyllithium ( sec ‐BuLi) and tetramethylethylenediamine (TMEDA) occurs regioselectively by S N 2 allylation. In contrast, the organolithium species can be transmetalated to the mixed zinc cuprate that undergoes regioselective S N 2′ allylations. Transmetalation to the organozinc chloride allows a Negishi‐type cross‐coupling reaction with aryl bromides using palladium catalysis with triphenylphosphine (PPh 3 ) as ligand. The chemistry was applied to a very short synthesis of 7‐prenylindole and of the alkaloid vasconine.