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07/12/18

Approaching Parts-Per-Billion Levels in Organocatalysis: Ben List and Co-workers Publish Breakthrough Results in “Nature Chemistry”

Approaching Parts-Per-Billion Levels in Organocatalysis: Ben List and Co-workers Publish Breakthrough Results in “Nature Chemistry”

Since its establishment as a field at the beginning of this century, organocatalysis has significantly advanced chemical synthesis in academia and industry. However, a common view suggesting that organocatalysts are generally less active than metal-based catalysts and enzymes still occasionally persists.

Prof. Benjamin List, Director at the Max-Planck-Institut für Kohlenforschung, and his research team now discovered that even sub-parts-per-million-levels (<1 ppm) of a new chiral organocatalyst enable very difficult carbon–carbon bond forming reactions. The organocatalyst efficiently promotes the asymmetric aldol reaction of silyl ketene acetals with ketones to afford chiral tertiary aldols in excellent stereoselectivity, a transformation which metal-based catalysts have typically failed to achieve. “The developed method is operationally simple, scalable, and the obtained products are highly valuable and can be readily derivatized. Generally, only a ppm level loading of the catalyst is required. We think that our discovery represents a major milestone, not only in the field of organocatalysis, but in chemical synthesis as a whole.”, List explains.

The research team led by Dr. Han Yong Bae describes their work in “Approaching sub-ppm-level asymmetric organocatalysis of a highly challenging and scalable carbon–carbon bond forming reaction” published in Nature Chemistry on July 9th 2018.

Photo: Dr. Han Yong Bae with Benjamin List in the lab.