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Catalytic Asymmetric Disulfuration by a Chiral Bulky Three-Component Lewis Acid-Base
Qi Zhang1,2, Yao Li3, Long Zhang3
1Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
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.
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