Acetophenone imine

A similar study on the deprotonation/silylation process of iV-benzyl acetophenone imine led to similar results. Again n-butyllithium was shown to be regioselective. A second deprotonation-trimethylsilylation sequence leads to the expected BSMA derivative.150... 

A series of 1-substituted indolines such as 79 has been synthesized via aryl radieal cyclizations of acetophenone imines 80, providing an enantioselective route to indoline a-amino acids <03JA163>. Aluminum chloride-induced cyclization of imine precursors derived by condensation of p-anisidine and a-phosphorylated-a-chloro aldehydes provided 3-phosphorylated 5-methoxyindoles <03CHE1521>. 

A novel, three-component, palladium-catalyzed, cascade cyclization-anion-capture process which involves in situ generation of a zipper molecule has been reported. Thus, 2-iodobenzoyl chloride, an acetophenone imine, and carbon monoxide react in the presence of Pd(PPh3)2Cl2 to give isoindolin-l-one in moderate yield (eq 86). 

Since there is great interest in compounds bearing quaternary stereocenters, soluble catalyst 25 was also applied to keto-imines in the presence of in situ generated HCN (Scheme 30.6) [17]. Whereas hydrocyanation adducts of N-allyl protected ketimines were prone to decompose via a retro-Strecker reaction, N-benzylated Strecker adducts 28 were obtained in mostly excellent yields and very high ee s. In general, acetophenone imines 27 were suitable substrates whereas aliphatic ketimines 27 showed a lowered optical purity. Although the benzyl protection group was necessary to obtain stable Strecker adducts 28, transformation of these adducts into amino acids was made more difficult. It could also be shown that... 

Condensation Reactions. Boron trichloride converts ketones into (Z)-boron enolates at —95 °C in the presence of Diisopropyl-ethylamine. These enolates react with aldehydes with high syn diastereoselectivity (eq 2). A similar condensation of imines with carbonyl compounds also provides crossed aldols in reasonable yields. The reaction was extended to the asymmetric aldoi condensation of acetophenone imine and benzaldehyde by using isobornylamine as a chiral auxiliary (48% ee). ... 

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