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The successful example of chiral formamides that function as asymmetric catalysts is described. (S,S)-N,N-Bis(α-methylbenzyl)formamide mediates the enantioselective addition of allyl- and crotyltrichlorosilanes to aliphatic aldehydes with the assistance of hexamethylphosphoramide (HMPA) to afford the corresponding homoallylic alcohols in up to 98% enantiomeric excess.
(S,S)-N,N-Bis(-α-methylbenzyl)formamide is the first example of chiral formamides that function as Lewis base catalysts to effectively serve catalytic asymmetric synthesis. The chiral formamide in combination with an additive, HMPA, catalyzes allylations of aliphatic aldehydes with allyl- and crotyltrichlorosilanes with high enantioselectivity (up to 98% ee). In the crotylations with (E)-crotyltrichlorosilane,...
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