A chiral formamide: Design and application to catalytic asymmetric synthesis

(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 crotyl...

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Bibliographic Details
Published in:Tetrahedron letters 1998-04, Vol.39 (18), p.2767-2770
Main Authors: Iseki, Katsuhiko, Mizuno, Shin, Kuroki, Yoshichika, Kobayashi, Yoshiro
Format: Article
Language:English
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Summary:(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. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)00334-7