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Stereoselective Protonation of Boron Enolates
Author(s) -
Haubenreich Thomas,
Hünig Siegfried,
Schulz HansJoachim
Publication year - 1993
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199303981
Subject(s) - protonation , trifluoroacetic acid , boron , acetic acid , chemistry , medicinal chemistry , stereoselectivity , organic chemistry , catalysis , ion
Due to the different coordinations of acetic acid and trifluoroacetic acid to the boron atom of the enolate 1 , two reaction mechanisms result for the protonation of 1 . The protonation with acetic acid leads to an enrichment of the ( R ) isomer ( R )‐ 2 . while with trifluoroacetic acid ( S ) ‐2 is favored. R * = isopinocampheyl.
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