Stereochemical studies-XIII. Cyclic aminoalcohols and related compounds-VI synthesis of the four 2-amino-4-t-butylcyclopentanol isomers

G. Bernáth, M. Svoboda

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Abstract

From diethyl 3-t-butyladipate (5), via cis- and trans-4-t-butylcyclopentene-1,2-oxide (31, 32) as key compounds, the syntheses of cis-2-amino-cis-4-t-butylcyclopentanol (1), cis-2-amino-trans-4-t-butylcyclopentanol (2), trans-2-amino-cis-4-t-butylcyclopentanol (3) and trans-2-amino-trans-4-t-butylcyclopentanol (4) have been achieved. 1, 3 and 4 were also synthesized from the corresponding 2-hydroxy-4-t-butylcarboxylic acids by Curtius degradation of the hydrazides (11, 18, 19). The steric course of process leading to the above compounds is discussed.

Original languageEnglish
Pages (from-to)3475-3484
Number of pages10
JournalTetrahedron
Volume28
Issue number13
DOIs
Publication statusPublished - 1972

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Isomers
Oxides
Degradation
Acids

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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Stereochemical studies-XIII. Cyclic aminoalcohols and related compounds-VI synthesis of the four 2-amino-4-t-butylcyclopentanol isomers. / Bernáth, G.; Svoboda, M.

In: Tetrahedron, Vol. 28, No. 13, 1972, p. 3475-3484.

Research output: Contribution to journalArticle

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