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Regiodivergent Addition of Carbon Units to Dual‐Activated Alkynes for Stereoselective Construction of Tetrasubstituted Alkenes
Author(s) -
Ueda Masafumi,
Matsubara Hiroshi,
Yoshida Kinichi,
Sato Aoi,
Naito Takeaki,
Miyata Okiko
Publication year - 2011
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/chem.201002744
Subject(s) - regioselectivity , stereoselectivity , chemistry , alkyl , electrophile , reagent , aryl , selectivity , adduct , addition reaction , cascade reaction , domino , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis
Switchable reaction : Reagent‐dependent regioselective additions to dual ‐ activated alkynes have been developed (see scheme; E=electrophile, R 1 =alkyl, R 2 =alkyl or aryl). The reaction with an alkyl radical afforded the β‐addition product, whereas the reaction with an organocuprate gave the α‐adduct with high regio‐ and stereoselectivities. These reactions were applied to domino and one‐pot reactions, providing tetrasubstituted and functionalized alkenes. Computational studies have been used to rationalize the selectivity.