Highly Efficient Alkylation to Ketones and Aldimines with Grignard Reagents Catalyzed by Zinc(II) Chloride
Manabu Hatano, Shinji Suzuki and Kazuaki Ishihara*
*Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan, Email: ishiharacc.nagoya-u.ac.jp
M. Hatano, S. Suzuki, K. Ishihara, J. Am. Chem. Soc., 2006, 128, 9998-9999.
DOI: 10.1021/ja0628405 (free Supporting Information)
A highly efficient Zn-catalyzed alkylation of ketones and aldimines with Grignard reagents via trialkylzinc(II) ate complexes minimizes problems with the use of only Grignard reagents, which leads to reduction and aldol side products, and the yield of desired alkylation products could be improved.
see article for more examples
proposed mechanism and transition-state assembly
M. Hatano, O. Ito, S. Suzuki, K. Ishihara, J. Org. Chem., 2010, 75, 5008-5016.