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200517.fm Page 30 Friday, March 18, 2005 2:52 PM
2005
Enantioselective syntheses
O 0031
(R)-1,1'-Binaphthyl-2-bis(pentafluorophenyl)borane Lewis Acids. — An efficient
of several boryl-substituted binaphthyls (I) is presented. These binaphthyls
17- 030 synthesis
serve as catalysts in the allylstannylation of aromatic aldehydes, e.g. (II), although only
low to moderate stereoselectivity is achieved. It is shown that steric factors at the
2'-position of the binaphthyl influence the stereoselectivity, and best results
(up to 34% e.e.) are obtained with the 2'-methylbinaphthylborane (Ib). —
(MORRISON, D. J.; PIERS*, W. E.; PARVEZ, M.; Synlett 2004, 13, 2429-2433;
Dep. Chem., Univ. Calgary, Calgary, Alberta T2N 1N4, Can.; Eng.) — Mischke
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