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Allylindation of Cyclopropenes in Organic and Aqueous Media: Switching the Regio‐ and Stereoselectivity Based on the Chelation with a Hydroxyl Group and the Crystal Structure of the Cyclopropylindium Product
Author(s) -
Araki Shuki,
Shiraki Fumio,
Tanaka Takashi,
Nakano Hiroyuki,
Subburaj Kandasamy,
Hirashita Tsunehisa,
Yamamura Hatsuo,
Kawai Masao
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010702)7:13<2784::aid-chem2784>3.0.co;2-a
Subject(s) - stereoselectivity , chemistry , chelation , reagent , aqueous solution , molecule , indium , crystal structure , group (periodic table) , medicinal chemistry , organic chemistry , stereochemistry , catalysis
Hydroxy‐bearing cyclopropenes react with allylindium reagents to undergo clean allylindation both in organic and aqueous media, in which the chelation of the hydroxyl group to indium plays the central role. The regio‐ and stereoselectivity have been regulated both by the location of the hydroxyl group in the molecules and the reaction solvents. In particular, the allylindation in water shows marked differences from that in organic solvents; the regio‐ and stereoselectivity have totally been reversed compared with those in organic solvents. Unusually stable cyclopropylindium compounds have been isolated from the reaction of 1‐( ω ‐hydroxyalkyl)cyclopropenes and the structure has fully been established by X‐ray crystallography.