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A Theoretical and Experimental Study of the Asymmetric Addition of Dialkylzinc to N ‐(Diphenylphosphinoyl)benzalimine
Author(s) -
Brandt Peter,
Hedberg Christian,
Lawonn Klaus,
Pinho Pedro,
Andersson Pher G.
Publication year - 1999
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/(sici)1521-3765(19990604)5:6<1692::aid-chem1692>3.0.co;2-m
Subject(s) - diethylzinc , diastereomer , enantioselective synthesis , bicyclic molecule , chemistry , selectivity , ton , catalysis , stereochemistry , medicinal chemistry , organic chemistry , biology , fishery
A transition state of type 1 is involved in the enantioselective addition of diethylzinc to N ‐(diphenylphosphinoyl)benzalimine with catalysis by bicyclic 2‐azanorbornyl‐3‐methanols. This was shown by quantum chemical calculations, which were also used to identify the factors responsible for the selectivity. An efficient route to both diastereomers of new bicyclic 2‐azanorbornyl‐3‐methanols with an additional chiral center was developed, and in the best case, up to 97 % ee was obtained with these ligands.