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Formation of Quaternary Carbon Centers by Highly Regioselective Hydroformylation with Catalytic Amounts of a Reversibly Bound Directing Group
Author(s) -
Ueki Yusuke,
Ito Hideto,
Usui Ippei,
Breit Bernhard
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.201101186
Subject(s) - hydroformylation , regioselectivity , alkyl , chemistry , carbon atom , aryl , catalysis , group (periodic table) , carbon fibers , organic chemistry , combinatorial chemistry , computer science , rhodium , algorithm , composite number
Directly opposing Keulemans rule! Phosphinites work as reversibly bound directing groups allowing for the first highly regioselective hydroformylation of 3‐substituted homoallylic alcohols to construct quaternary carbon centers. This method enables the atom‐economical synthesis of a wide range of α,α‐disubstituted γ‐lactones and highly substituted tetrahydrofurans (see scheme; R 1 , R 2 =alkyl/aryl).