Synfacts 2011(6): 0672-0672  
DOI: 10.1055/s-0030-1260429
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Efficient Hydrogen-Bond Catalysis with (Thio)Phosphorodiamides

Contributor(s): Benjamin List, Olga Lifchits
R. Wu, X. Chang, A. Lu, Y. Wang*, G. Wu, H. Song, Z. Zhou*, C. Tang
Nankai University, Tianjin, P. R. of China
Further Information

Publication History

Publication Date:
19 May 2011 (online)

Significance

Wang, Zhou and colleagues report a novel double hydrogen-bonding catalyst 1 based on the (thio)phosphorodiamide core. Like the Takemoto catalyst 2, compound 1 was made bifunctional by the inclusion of a basic tertiary amine. Crystallographic analysis of 1 revealed that the distance between the two acidic H atoms is 1.1 and 0.5 Å greater than in the Takemoto catalyst 2 and the recently developed squaramide ­catalyst 3, respectively. Michael addition of 2-­hydroxy-1,4-napthoquinone 4 to nitroolefins 5 was chosen as the model reaction. Impressively, almost perfect enantioselectivity was achieved for essentially all substrates.