Facile Enantioselective Ring‐Opening Reaction of meso Epoxides with Anilines Using (S)‐(–)‐BINOL‐Ti Complex as a Catalyst

The catalytic enantioselective ring‐opening reaction of meso‐stilbene oxide and cyclohexene oxide with anilines was catalyzed by (S)‐(–)‐BINOL‐Ti complexes at ambient temperature to obtain β‐amino alcohols in high yield (95 %) and enantioselectivity (ee, 78 %). The enantiomeric excess (ee) of the product was further improved to 98 % by a single recrystallization step. The absolute configuration of representative β‐amino alcohols was determined by single‐crystal X‐ray diffraction analysis. The catalyst recovered after first use was recycled four times with retention in its performance. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)