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Study of the Configuration Stability of the Carbon – Zinc Bond, Direct Measurement of Enantiomeric Ratios, and Tentative Assignment of the Absolute Configuration in Secondary Organozinc Halides
Author(s) -
Guijarro Albert,
Rieke Reuben D.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000417)39:8<1475::aid-anie1475>3.0.co;2-s
Subject(s) - absolute configuration , halide , zinc , enantiomer , chemistry , inorganic chemistry , stereochemistry , organic chemistry
A straightforward way to determine enantiomeric ratios and predict absolute configurations in organozinc reagents is possible by the use of (+)‐2,2′‐isopropylidene‐bis(( R )‐4‐phenyloxazoline) ((+)‐ 1 ) and its racemic counterpart (±)‐ 1 as chiral solvating agents for NMR spectroscopy. The signals corresponding to the α ‐hydrogen atom (relative to the zinc atom) in a secondary organozinc bromide and its evolution after chiral (left) and racemic (right) complexation are shown.