Organic Chemistry Seminar

This talk will be focused on our adventure in asymmetric nucleophilic phosphine catalysis. Recently, we designed a series of bifunctional phosphines based amino acid structural motifs. Our phosphine catalysts can be readily prepared, and their structures are highly tunable. Moreover, such phosphine catalysts possess excellent stability, and can be used directly for reactions without protection of inert gas. Up to date, we have successfully applied our phosphine catalysts to enantioselective aza-Morita-Baylis-Hillman (MBH) & MBH reactions, a range of [3+2] cycloadditions, different [4+2] cycloadditions, [4+1] annulation, allylic alkylations, Michael addition, and g-addition reactions. The details of our investigations will be presented, and some mechanistic understandings will also be discussed.

Selected References:

1.    Yao, W.; Dou, X.; Lu, Y. J. Am. Chem. Soc., 2015, 137, 55.

2.    X. Han, W. Yao, T. Wang, Y. R. Tan, Z. Yan, J. Kwiskowski, Y. Lu, Angew. Chem. Int. Ed. 2014, 53, 5643.

2.    T. Wang, W. Yao, F. Zhong, G. H. Pang, Y. Lu, Angew. Chem. Int. Ed. 2014, 53, 2964.

3.    F. Zhong, X. Dou, X. Han, W. Yao, Q. Zhu, Y. Meng, Y. Lu, Angew. Chem. Int. Ed. 2013, 52, 943

4.    F. Zhong, J. Luo, G.-Y. Chen, X. Dou, Y. Lu, J. Am. Chem. Soc. 2012, 134, 10222.

5.    X. Han, F. Zhong, Y. Wang, Y. Lu, Angew. Chem. Int. Ed. 2012, 51, 767.

6.    F. Zhong, X. Han, Y. Wang, Y. Lu, Angew. Chem. Int. Ed. 2011, 50, 7837.

7.    X. Han, Y. Wang, F. Zhong, Y. Lu, J. Am. Chem. Soc. 2011, 133, 1726.