Enantio- and diastereoselective synthesis of piperidines by coupling of four components in a "one-pot" sequence involving diphenylprolinol silyl ether mediated michael reaction

Tatsuya Urushima, Daisuke Sakamoto, Hayato Ishikawa, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

82 Citations (Scopus)

Abstract

An efficient, asymmetric, four-component, one-pot synthesis of highly substituted piperidines with excellent diastereo- and enantioselectivity was established through the diphenylprolinol silyl ether mediated Michael reaction of aldehyde and nitroalkene, followed by the domino aza-Henry reaction/hemiaminalization reaction and a Lewis acid mediated allylation or cyanation reaction. All carbons of the piperidine ring are substituted with different groups, and its five contiguous stereocenters are completely controlled in both relative and absolute senses.

Original languageEnglish
Pages (from-to)4588-4591
Number of pages4
JournalOrganic letters
Volume12
Issue number20
DOIs
Publication statusPublished - 2010 Oct 15

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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