cas 147227-26-7, ALPHA,ALPHA-BIS(TRIMETHYLSILYL)-TERT-BUTYLKETIMINE | Articles data ｜lookchem

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147227-26-7

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A convenient route to (E)-α,β-unsaturated methyl ketones
Aldehydes are converted into (E)-α,β-unsaturated methyl ketones in good yield and with a high E stereoselectivity using α,α- bis(trimethylsilyl) N-tert-butyl acetimine 3. The reaction was mediated by a catalytic amount of tetrabutylammonium fluoride (TBAF) under mild conditions. The disilylated reagent 3 is easily generated from N-tert-butylacetimine, lithium diisopropylamide (LDA), and chlorotrimethylsilane. The mechanism of the reaction is discussed. Copyright
Bellassoued,Aatar,Bouzid,Damak
experimental part
p. 1886 - 1895
(2010/11/18)

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.
Bellassoued, Moncef,Majidi, Assieh
p. 2517 - 2522
(2007/10/02)

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Chemical Properties

Boiling Point: 104 °C (8 mmHg)
Storage Temp.:0-6°C
Refractive Index: 1.4505-1.4525
PSA: 23.85000
LogP: 4.73780

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