Novel route to the synthesis of hydroxylated piperidine and pyrrolidine derivatives via the intramolecular reaction of γ-aminoallylstannane with aldehyde

Isao Kadota, Miho Kawada, Shioko Saya, Yoshinori Yamamoto

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The Lewis acid mediated intramolecular reaction of gamma-aminoallyl-stannane 6 gave trans-beta-hydroxypiperidine derivative 7a as a major product. On the other hand, the thermal cyclization of 6 and 8 afforded cis-beta-hydroxypiperidine 7b and pyrrolidine derivative 9b, respectively, with very high stereoselectivity.

Original languageEnglish
Pages (from-to)2109-2112
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number12
DOIs
Publication statusPublished - Mar 18 1996
Externally publishedYes

Fingerprint

Lewis Acids
Cyclization
Aldehydes
Hot Temperature
Derivatives
Stereoselectivity
pyrrolidine
stannane
piperidine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Novel route to the synthesis of hydroxylated piperidine and pyrrolidine derivatives via the intramolecular reaction of γ-aminoallylstannane with aldehyde. / Kadota, Isao; Kawada, Miho; Saya, Shioko; Yamamoto, Yoshinori.

In: Tetrahedron Letters, Vol. 37, No. 12, 18.03.1996, p. 2109-2112.

Research output: Contribution to journalArticle

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