Stereoselective synthesis of erythro α-amino epoxides

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Abstract

The stereoselective reduction of bromomethyl ketones derived from leucine, phenylalanine, alanine and valine is described using borohydride reagents. The Boc-amino alcohol product has erythro stereochemistry at the carbinol center as deduced by conversion to Boc-amino epoxides. These oxiranes are useful for the preparation of hydroxyethylene peptide isosteres.

Original languageEnglish
Pages (from-to)5453-5456
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number31
DOIs
StatePublished - 31 Jul 1995

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Epoxy Compounds
Amino Alcohols
Borohydrides
Stereochemistry
Valine
Ketones
Phenylalanine
Leucine
Alanine
Methanol
Peptides
hydroxyethylene

Cite this

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title = "Stereoselective synthesis of erythro α-amino epoxides",
abstract = "The stereoselective reduction of bromomethyl ketones derived from leucine, phenylalanine, alanine and valine is described using borohydride reagents. The Boc-amino alcohol product has erythro stereochemistry at the carbinol center as deduced by conversion to Boc-amino epoxides. These oxiranes are useful for the preparation of hydroxyethylene peptide isosteres.",
author = "David Rotella",
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Stereoselective synthesis of erythro α-amino epoxides. / Rotella, David.

In: Tetrahedron Letters, Vol. 36, No. 31, 31.07.1995, p. 5453-5456.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Rotella, David

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AB - The stereoselective reduction of bromomethyl ketones derived from leucine, phenylalanine, alanine and valine is described using borohydride reagents. The Boc-amino alcohol product has erythro stereochemistry at the carbinol center as deduced by conversion to Boc-amino epoxides. These oxiranes are useful for the preparation of hydroxyethylene peptide isosteres.

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