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Water Freezing as a Regiocontrol Element in the Multicomponent Assembly of Cyclic Enones
Author(s) -
De la Campa Raquel,
Flórez Josefa
Publication year - 2015
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.201404670
Subject(s) - regioselectivity , moiety , chemistry , intramolecular force , anhydrous , allene , lithium (medication) , acetamide , organic chemistry , medicine , endocrinology , catalysis
Regioselective synthesis of dialkoxy 2‐cyclopentenones and 2‐cyclohexenones with novel substitution patterns has been accomplished by the one‐pot combination of three simple starting materials (chromium carbene complex, Weinreb acetamide lithium enolate and 1‐alkoxyallenyllithium) under either anhydrous conditions or water‐promoted solidification of the reaction mixture. These results revealed an unprecedented water‐freezing effect that plays a key role to completely reverse the regioselectivity of the intramolecular carbometalation of an allene moiety.