caa a22 4500 378923005 CHVBK 20180305123610.0 cr unu---uuuuu 161128e20040101xx s 000 0 eng 10.1351/pac200476030615 doi (NATIONALLICENCE)gruyter-10.1351/pac200476030615 Mechanistic insights into perfluoroaryl borane-catalyzed allylstannations: Toward asymmetric induction with chiral boranes [Elektronische Daten] [D. J. Morrison, J. M. Blackwell, W. E. Piers] The perfluoroaryl borane B(C6F5)3 is an effective catalyst for a variety of organic transformations. In the hydrosilation of carbonyl functions, it activates the silane rather than the carbonyl substrate. In allylstannation reactions, two competing reaction pathways are observed, one involving tin cation catalysis, the other "true" borane catalysis. For B(C6F5)3, the former mechanism dominates, while for the weaker Lewis acid PhB(C6F5)2, the latter pathway is more prominent. Thus, chiral boranes of similar Lewis acid strength to PhB(C6F5)2 have the potential to mediate asymmetric allylstannation of aldehyde substrates. © 2013 Walter de Gruyter GmbH, Berlin/Boston Morrison D. J. Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta T2N 1N4, Canada aut Blackwell J. M. Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta T2N 1N4, Canada aut Piers W. E. Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta T2N 1N4, Canada aut Pure and Applied Chemistry De Gruyter 76/3(2004-01-01), 615-623 0033-4545 76:3<615 2004 76 pac https://doi.org/10.1351/pac200476030615 text/html Onlinezugriff via DOI 1 research article jats NATIONALLICENCE 856 40 https://doi.org/10.1351/pac200476030615 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Morrison D. J. Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta T2N 1N4, Canada aut NATIONALLICENCE 700 1- Blackwell J. M. Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta T2N 1N4, Canada aut NATIONALLICENCE 700 1- Piers W. E. Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta T2N 1N4, Canada aut NATIONALLICENCE 773 0- Pure and Applied Chemistry De Gruyter 76/3(2004-01-01), 615-623 0033-4545 76:3<615 2004 76 pac CC0 http://creativecommons.org/publicdomain/zero/1.0 nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-gruyter