Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5218713 | Tetrahedron | 2012 | 6 Pages |
Abstract
We have investigated the mechanism of chiral induction in the asymmetric [2,3]-Wittig rearrangement of allyl benzyl ether in the presence of a bis(oxazoline) chiral ligand [(S,S)-Box-tBu] by comparing the reaction of both enantiomers of monodeuterated benzyl ether 1a-d. As a result, we found that chirality was induced via enantioselective deprotonation followed by efficient chirality transfer of the resulting chiral benzyl carbanion with the inversion of stereochemistry. It was revealed that the chiral ligand facilitates selective deprotonation as well as prevents the chiral carbanion from racemization. Moreover, we examined the effect of the o-methoxy substituent on the benzene ring.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Maria Kitamura, Yoshimi Hirokawa, Yuki Yoshioka, Naoyoshi Maezaki,