Catalytic Asymmetric Disulfuration by a Chiral Bulky Three-Component Lewis Acid-Base

Qi Zhang; Yao Li; Long Zhang; Sanzhong Luo

doi:10.1002/anie.202101569

Catalytic Asymmetric Disulfuration by a Chiral Bulky Three-Component Lewis Acid-Base

Angew Chem Int Ed Engl. 2021 May 3;60(19):10971-10976. doi: 10.1002/anie.202101569. Epub 2021 Apr 6.

Authors

Qi Zhang^{1

2}, Yao Li³, Long Zhang³, Sanzhong Luo³

Affiliations

¹ Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
² Department of Chemistry, University of Chinese Academy of Sciences, Beijing, 100490, China.
³ Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing, China.

PMID: 33660896
DOI: 10.1002/anie.202101569

Abstract

A three-component Lewis acid-base (Lewis trio) involving a bulky chiral primary amine, B(C₆ F₅ )₃ and a bulky tertiary amine has been developed as an effective enamine catalyst for enantioselective disulfuration reactions. The bulky tertiary amine was found to activate a bulky primary-tertiary diamine-borane Lewis pair for enamine catalysis via frustrated interaction. The resulted chiral bulky Lewis trio (BLT) allows for the construction of chiral disulfides via direct disulfuration with β-ketocarbonyls or α-branched aldehydes in a practical and highly stereocontrolled manner.

Keywords: chiral primary amines; disulfuration; enamines; frustrated Lewis pairs; organocatalysis.

Grants and funding

National Natural Science Foundation of China