147227-27-8

Upstream product

• 39511-08-5 (E)-3-(2-furanyl)-2-propenal 
• 127896-07-5 α,α-bis(trimethylsilyl)-tert-butylacetaldehyde imine 
• 98-01-1 furfural 
• 147608-67-1 γ-trimethylsilyl-N-tert-butylcrotonaldimine 
• 6943-47-1 1-tert-butyl-4-methyl-1-aza-1,3-butadiene 
• 100-52-7 benzaldehyde 

Downstream Products

• 13466-40-5 (2E, 4E)-5-phenylpenta-2,4-dienal 

Relevant academic research and scientific papers

A Simple and Highly Stereoselective Route to E-α,β-Unsaturated Aldehydes

Zinc bromide mediated reaction of α,α-bis(trimethylsilyl)-tert-butylacetaldimine (3) with a wide range of aldehydes takes place under mild conditions and affords the corresponding α,β-unsaturated aldehydes in good yields and with high E stereoselectivity (>98percent).This procedure is successfully applied to the preparation of intermediates for retinoid and natural product synthesis.

Exclusive γ-regio functionalization of crotonaldehyde using γ-trimethylsilyl crotonaldimine. Application to the one pot synthesis of conjugated dienals

Cesium fluoride mediated reaction of γ-trimethylsilyl N-tert-butyl crotonaldimine 9 with a wide range of aldehydes takes place in DMSO at room temperature and affords exclusive γ-regio functionalized products. Heating (rt to 100°C) the δ-silyloxy imines 11 thus obtained leads, after very mild hydrolysis of the tert-butylimine function, to the conjugated dienals 14 in good yields and with excellent (E,E)-selectivities.

A new and easy route to (2E,4E)-dienals by four-carbon homologation of aldehydes

A new synthetic method of (2E,4E)-dienals by four-carbon homologation of aldehydes is described. γ-trimethylsilyl crotonaldimine 2 , easily generated from N-ter-butyl-crotonaldimine 1, LDA and ClSiMe3, reacts with aldehydes in the presence of catalytic CsF in DMSO at rt → 100°C to afford homologous aldehydes 3 in good yields and with excellent (E,E)-selectivities.