Diastereo- and enantioselective synthesis of β-amino cyclic ethers via the intramolecular reaction of γ-alkoxyallylstannane with imine

Jung Youl Park, Isao Kadota, Yoshinori Yamamoto

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The intramolecular Lewis acid mediated cyclization of γ- alkoxyallylstannanes 1, 2, and 14, bearing a hydrazone group at the terminus of the carbon chain, afforded exclusively the corresponding trans β-amino cyclic ethers 3a, 4a, and 15, respectively. The Lewis acid mediated cyclization of Γ-alkoxyallylstannane 5, having (R)-(+)-1-phenylethylamine as a chiral auxiliary, afforded exclusively, trans ̄-amino cyclic ether 6a with very high diastereomeric excess (de) in very high chemical yields. The asymmetric cyclization of Γ-alkoxyallylstannane with imine 7 in the presence of chiral titanium-BINOL complex 9, afforded predominantly cis β-amino cyclic ether 8b with high enantiomeric excess (ee). The chiral Lewis acid mediated cyclization of racemic compound 38 containing phenyl as a substituent afforded cis isomer 39 with very high enantiomeric excess (ee).

Original languageEnglish
Pages (from-to)4901-4908
Number of pages8
JournalJournal of Organic Chemistry
Volume64
Issue number13
DOIs
Publication statusPublished - Jun 25 1999
Externally publishedYes

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Cyclic Ethers
Imines
Cyclization
Lewis Acids
Bearings (structural)
Phenethylamines
Hydrazones
Titanium
Isomers
Carbon

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Diastereo- and enantioselective synthesis of β-amino cyclic ethers via the intramolecular reaction of γ-alkoxyallylstannane with imine. / Park, Jung Youl; Kadota, Isao; Yamamoto, Yoshinori.

In: Journal of Organic Chemistry, Vol. 64, No. 13, 25.06.1999, p. 4901-4908.

Research output: Contribution to journalArticle

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