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

摘要

Treatment of 1-chlorovinyl p-tolyl sulfoxides, prepared from ketones and chloromethylp-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 alpha-quaternary alpha-amino aldehydes in good yields. From alpha-quaternary alpha-amino aldehydes, alpha-quatemary alpha-amino acid esters and beta-quaternary beta-amino alcohols were obtained. When optically active chloromethyl p-tolyl sulfoxide was used in this procedure, a method for the synthesis of optically active alpha-quaternary a-amino aldehydes was realized. The reaction mechanism, including asymmetric induction, for the formation of the sulfinylaziridines is described. (C) 2007 Elsevier Ltd. All rights reserved.