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Magnesium(II)-Binaphtholate as a Practical Chiral Catalyst for the Enantioselective Direct Mannich-Type Reaction with Malonates

Manabu Hatano, Takahiro Horibe and Kazuaki Ishihara*

*Graduate School of Engineering, Nagoya University, and CREST, Japan Science and Technology Agency (JST), Furo-cho, Chikusa, Nagoya 464-8603, Japan, Email: ishiharacc.nagoya-u.ac.jp

M. Hatano, T. Horibe, K. Ishihara, Org. Lett., 2010, 12, 3502-3505.

DOI: 10.1021/ol101353r (free Supporting Information)



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Abstract

In a highly enantioselective direct Mannich-type reaction of aldimines with dialkyl malonates, an inexpensive Mg(II)-BINOLate salt can activate both aldimines and malonates as a cooperative acid-base catalyst. Various β-aminoesters and α-halo-β-aminoesters could be synthesized in high yields and with high enantioselectivities even in gram-scale.

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Chiral Lithium(I) Binaphtholate Salts for the Enantioselective Direct Mannich-Type Reaction with a Change of Syn/Anti and Absolute Stereochemistry

M. Hatano, T. Horibe, K. Ishihara, J. Am. Chem. Soc., 2010, 132, 56-57.


Key Words

β-Amino Acids, Mannich Reaction


ID: J54-Y2010-2140