A synthesis, including asymmetric synthesis, of α-quaternary α-amino aldehydes from ketones and chloromethyl p-tolyl sulfoxide via sulfinylaziridines

Add time:08/16/2019    Source:sciencedirect.com

Treatment of 1-chlorovinyl p-tolyl sulfoxides, prepared from ketones and chloromethyl p-tolyl sulfoxide, with N-lithio arylamines resulted in the formation of sulfinylaziridines in good to high yields. The sulfinylaziridines were treated with N-lithio aniline or N-lithio p-chloroaniline to afford α-quaternary α-amino aldehydes in good yields. From α-quaternary α-amino aldehydes, α-quaternary α-amino acid esters and β-quaternary β-amino alcohols were obtained. When optically active chloromethyl p-tolyl sulfoxide was used in this procedure, a method for the synthesis of optically active α-quaternary α-amino aldehydes was realized. The reaction mechanism, including asymmetric induction, for the formation of the sulfinylaziridines is described.

We also recommend Trading Suppliers and Manufacturers of Ethyl β-Chlorovinyl Ketone (cas 105-32-8). Pls Click Website Link as below: cas 105-32-8 suppliers

Prev:Stereoselective aldol reactions of β-chlorovinyl ketones using dienol borinates: A new synthesis of dihydropyrones.
Next:Catalyzed addition of acid chlorides to alkynes by unmodified nano-powder magnetite: synthesis of chlorovinyl ketones, furans, and related cyclopentenone derivatives)