The inexpensive additive N-methylmorpholine effectively decreases the equivalents of nucleophiles in the catalytic highly enantioselective arylation of aryl aldehydes

Pei Wang; Yue Liu; Ya-Lun Zhang; Chao-Shan Da

doi:10.1002/chir.22709

The inexpensive additive N-methylmorpholine effectively decreases the equivalents of nucleophiles in the catalytic highly enantioselective arylation of aryl aldehydes

Chirality. 2017 Aug;29(8):443-450. doi: 10.1002/chir.22709. Epub 2017 May 25.

Authors

Pei Wang¹, Yue Liu¹, Ya-Lun Zhang¹, Chao-Shan Da^{1

2}

Affiliations

¹ Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, China.
² State Key Laboratory of Organic Chemistry, Lanzhou University, Lanzhou, China.

PMID: 28543685
DOI: 10.1002/chir.22709

Abstract

Highly enantioselective arylation of aryl aldehydes catalyzed by (S)-H₈ -BINOL-Ti(Oi-Pr)₂ complex in the presence of N-methylmorpholine (NMM) as an effective and inexpensive additive is described for the first time. We found high enantioselectivity and yield but successfully reduced the equivalents of nucleophiles triarylaluminums by 50% compared with our previous report. The practicability of the process was thereby greatly increased.

Keywords: NMM; aryl aldehydes; arylation; asymmetric catalysis; triarylaluminum.