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Pure Appl. Chem., 2012, Vol. 84, No. 11, pp. 2417-2430

Published online 2012-08-28

Boron-based pronucleophiles in catalytic (asymmetric) C(sp3)–allyl cross-couplings

Uwe Schneider*, Yi-Yong Huang, Ananya Chakrabarti, Hai Thanh Dao, Naohide Morita and Shū Kobayashi*

Department of Chemistry, School of Science, The University of Tokyo, Hongo, 7-3-1 Bunkyo-ku, Tokyo 113-0033, Japan

Abstract: Allylic and allenyl boronates or boranes were uncovered as suitable pronucleophiles in catalytic C–C bond formations with C(sp3) electrophiles such as O,O-acetals and N,O-aminals or ethers and carbohydrates. These transformations were most efficiently catalyzed by In(I) triflate. Importantly, chiral counteranion-directed, catalytic asymmetric allylation and allenylation of N,O-aminals was developed by employing a catalyst system composed of In(I) chloride and a chiral silver 2,2'-dihydroxy-1,1'-binaphthalene (BINOL)-phosphate.