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[2,3] Wittig Rearrangements of Nonconjugated Secondary α‐Lithioethers: Proof of Stereospecificity and Inversion of the Configuration of the Carbanion C Atom
Author(s) -
Hoffmann Rolf,
Brückner Reinhard
Publication year - 1992
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.199206471
Subject(s) - carbanion , stereospecificity , diastereomer , chemistry , stereoselectivity , walden inversion , wittig reaction , carbon atom , stereochemistry , organic chemistry , catalysis , ring (chemistry)
A stereoselective [2,3] Wittig rearrangement from the racemic α‐lithioether syn ‐ 1 , obtained from tin/lithium exchange in the corresponding α‐(tributylstannyl)ether, provides the configuratively uniform homoallyl alcohol anti ‐ 2 . The α‐lithioether diastereomeric to syn ‐ 1 rearranges just as stereoselectively to the diastereomer of anti ‐ 2 . The rearrangements are thus stereospecific and proceed with inversion of configuration on the carbanion carbon atom.