Reactions of Carbonyl Compounds with Heteroatom Nucleophiles

Reactions of Carbonyl Compounds with Heteroatom Nucleophiles 

As demonstrated in the pioneering works by Noyori and coworkers [7c,e], silyl tri-flates act as effective catalysts of acetalization of carbonyls with oxygen nucleophiles. Townsend and coworkers have successfully utilized the i-Pr3SiOTf-mediated 

The formation of N-acylpyridinium ions from acyl chlorides and pyridines is effectively promoted by (la) and i-Pr3SiOTf. The N-acylpyridinium ions are usable for the synthesis of dihydropyridines and their derivatives by alkylation with Grignard reagents [128]. This reaction sequence has been applied to asymmetric alkylation of pyridines using a chiral acyl chloride [129]. 

Silicon Lewis acids have been frequently used for deprotection of carbamates to amines, which can be assisted by protic, nucleophilic reagents or solvents such as alcohols and thiols [131, 132]. 

RsSiX-Promoted Reactions of I mines, Aminoacetals, and Related Compounds 

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