Diastereoselective electrophilic α-amination of camphor N1-acyl N2-phenylpyrazolidinones: the metal enolate-dependent synthesis of two possible hydrazide diastereomers

Chin Sheng Chao, Chung Kai Cheng, Ssu Hsien Li, Kwunmin Chen

研究成果: 雜誌貢獻文章同行評審

11 引文 斯高帕斯(Scopus)

摘要

Complementary approaches under enolate amination reactions for the synthesis of both α-hydrazidoacyl diastereomers have been achieved. Both isomers are obtained with high to excellent chemical yields and high stereoselectivities (up to >95:5 dr) when aryl-substituted camphor N1-acyl N2-phenylpyrazolidinone was treated with potassium hexamethyldisilylamide (KHMDS) and lithium hexamethyldisilylamide (LHMDS), respectively, followed by the addition of di-tert-butyl azodicarboxylate. The nondestructive removal of the chiral auxiliary, which can be carried out under mild condition, afforded the hydrazido alcohol with high enantiomeric ratio. The facial stereoselectivity and stereochemical course of the reactions are discussed.

原文英語
頁(從 - 到)333-336
頁數4
期刊Tetrahedron Letters
50
發行號3
DOIs
出版狀態已發佈 - 2009 一月 21

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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