Solvent‐Dependent Enantiodivergent Mannich‐Type Reaction: Utilizing a Conformationally Flexible Guanidine/Bisthiourea Organocatalyst

Yoshihiro Sohtome, Shinji Tanaka, Keisuke Takada, Takahisa Yamaguchi, Kazuo Nagasawa

Angewandte Chemie International Edition · 2010 · 161 citations · 55 references

Concepts

Abstract

Flex control: Malonate and tert-butoxycarbonyl (Boc)-protected imines react in the presence of the flexible catalyst 1 to furnish the S or the R adduct depending upon the solvent used. Kinetic analyses in this enantiodivergent organocatalysis show that enthalpy–entropy compensation explains this behavior.

References

55