Journal
CHIRALITY
Volume 22, Issue 1, Pages 88-91Publisher
WILEY
DOI: 10.1002/chir.20710
Keywords
bismuth bromide; chiral alcohols; configuration determination; heterogeneous catalysis; benzylic ethers; protecting groups
Funding
- Ministero dell'Istruzione dell'Universiti e della Ricerca (MIUP, PRIN)
- Consiglio Nazionale delle Ricerche (CNR)
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Chiral reactants have been employed for assessing the real stereochemistry of the BiBr3-catalyzed synthesis of benzylic ethers, a very useful reaction for protecting alcoholic groups. The results of this investigation are in clear contrast with the conclusions of previous studies (Boyer et al., Tetrahedron 2001;57:1917-1921). Indeed, chiral GC-MS analysis of the ethereal products gives unequivocal evidence of the complete racemization of the benzylic moiety and the complete retention of configuration of the protected alcoholic substrate. Such findings make BiBr3 a powerful and stereo-chemically preservative catalyst for benzylation of chiral alcohols, and a potential candidate for orthogonal protecting group strategies applicable to polyhydroxy compounds. Chirality 22:88-91, 2010. (C) 2009 Wiley-liss, Inc.
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