A synthesis, including asymmetric synthesis, of α-quaternary α-amino aldehydes from ketones and chloromethyl p-tolyl sulfoxide via sulfinylaziridines
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.
展开
关键词:
STEREOSELECTIVE-SYNTHESIS ACID DERIVATIVES CARBON CENTERS CYCLIC-KETONES ENANTIOSELECTIVE CONSTRUCTION CONJUGATE ADDITION ORGANIC-SYNTHESIS BETA-POSITION 3 COMPONENTS ESTERS
DOI:
10.1016/J.TET.2007.03.067
年份:
2007


通过文献互助平台发起求助,成功后即可免费获取论文全文。
相似文献
参考文献
引证文献
来源期刊
辅助模式
引用
文献可以批量引用啦~
欢迎点我试用!