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A chiral formamide: Design and application to catalytic asymmetric synthesis

✍ Scribed by Katsuhiko Iseki; Shin Mizuno; Yoshichika Kuroki; Yoshiro Kobayashi

Book ID
104259053
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
283 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

S,S)-H,N-Bis(-a-methylbenzyl)formamide is the first example of chiral formamides that function as Lewis base catalysts to effectively serve catalytic asymmetric synthesis. The chiral fommamide in combivmlon with an additive, HMPA, catalyzes allylations of aliphatJc aldehydes with allyi-and crotyltric~ with high enantioselcctivity (up to 98% co). In the crotylafions with (E)crotyltrichlot'osilane, cyclohexanecarboxaldehyde and hydrocinnamaldehyde gave the ~m, esponding anti homoallylic alcohols exclusively with 98 and 94% ee's, respectively.

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