K. Iseki, S. Mizuno, Y. Kuroki
Apr 30, 1998
Citations
0
Influential Citations
67
Citations
Journal
Tetrahedron Letters
Abstract
Abstract ( S , S )- N , N -Bis(-α-methylbenzyl)formamide is the first example of chiral formamides that function as Lewis base catalysis 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, cyclohexanecarboxaldehyde and hydrocinnamaldehyde gave the corresponding anti homoallylic alcohols exclusively with 98 and 94% ee's, respectively.