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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 24
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Original Articles

Novel Chiral Bisformamide-Promoted Asymmetric Allylation of Benzaldehyde with Allyltrichlorosilane

, , &
Pages 3627-3634 | Received 07 Sep 2010, Published online: 22 Aug 2011
 

Abstract

Novel chiral bisformamides have been prepared from (R,R)-1,2-cyclohexanediamine and utilized as Lewis bases in the asymmetric allylation of benzaldehyde with allyltrichlorosilane. The reaction in the presence of Lewis base 1i gave an 83:17 enantiomeric ratio (R/S) of the products in 90% isolated yield.

Notes

a Reaction performed with 0.5 mmol of Lewis base, 0.5 mmol of benzaldehyde, and 1.5 mmol of allylsilane in dichloromethane (2 mL) at −78 °C for 3 days.

b Determined by Daicel Chiralcel OD (n-hexane/i-PrOH = 19/1).

c Isolated yields after column chromatography.

a Reaction performed with Lewis base (0.5 mmol or 2.5 mmol), 0.5 mmol of benzaldehyde, and 1.5 mmol of allyltrichlorosilane in dichloromethane (2 mL) at −78 °C for 3 days.

b Determined by Daicel Chiralcel OD (n-hexane/i-PrOH = 19/1).

c Isolated yields after column chromatography (n-hexane/dichloromethane = 2/1).

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