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

A three-component Lewis acid-base (Lewis trio) involving a bulky chiral primary amine, B(C6F5)(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 beta-ketocarbonyls or alpha-branched aldehydes in a practical and highly stereocontrolled manner.

Automated summary

A novel three-component Lewis acid-base catalyst has been developed, utilizing a bulky tertiary amine to activate a Lewis pair for enamine catalysis, allowing for asymmetric control of disulfuration reactions.