Asymmetric allylboration of aldehydes and ketones using 3,3'-disubstitutedbinaphthol-modified boronates.
Allylboronates derived from 3,3'-disubstituted 2,2'-binaphthols react with aldehydes and ketones to give the expected allylated products with up to >99:1 er. Highest selectivities were observed for aromatic ketones. The bis(trifluoromethyl) derivative is particularly outstanding in terms of reactivity, selectivity, and robustness. [reaction: see text]
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, (GWC), Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1.
T Robert
TR
Wu
Lixin
L
Shen
J Michael
JM
Chong