[2,3] WITTIG REARRANGEMENTS OF NONCONJUGATED SECONDARY ALPHA-LITHIOETHERS - PROOF OF STEREOSPECIFICITY AND INVERSION OF THE CONFIGURATION OF THE CARBANION-C ATOM

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. (Figure Presented.) Copyright © 1992 by VCH Verlagsgesellschaft mbH, Germany