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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

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, J. Am. Chem. Soc., 2010, 132, 56-57.

DOI: 10.1021/ja909874b (free Supporting Information)


Abstract

Li(I) BINOLate salts as Lewis acid-Brønsted base catalysts offer high catalytic activity toward 1,3-dicarbonyl compounds such as diketone, ketoester, ketothioester, ketoamide, and ketolactone. Mannich-type reaction of aldimines with 1,3-dicarbonyl compounds proceeded at -78 °C within 1-2 h in the presence of 1−10 mol % catalyst highly enantio- and diastereoselectively.

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

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


Key Words

β-Amino Acids, Mannich Reaction


ID: J48-Y2010-0100