Stereoselective synthesis of erythro α-amino epoxides

David P. Rotella

doi:10.1016/00404-0399(50)1087X-

Stereoselective synthesis of erythro α-amino epoxides

David P. Rotella

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

57 Scopus citations

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 language	English
Pages (from-to)	5453-5456
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	31
DOIs	https://doi.org/10.1016/00404-0399(50)1087X-
State	Published - 31 Jul 1995

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10.1016/00404-0399(50)1087X-

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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 = "Rotella, {David P.}",

year = "1995",

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T1 - Stereoselective synthesis of erythro α-amino epoxides

AU - Rotella, David P.

PY - 1995/7/31

Y1 - 1995/7/31

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0029146889&partnerID=8YFLogxK

U2 - 10.1016/00404-0399(50)1087X-

DO - 10.1016/00404-0399(50)1087X-

M3 - Article

AN - SCOPUS:0029146889

SN - 0040-4039

VL - 36

SP - 5453

EP - 5456

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

Stereoselective synthesis of erythro α-amino epoxides

Abstract

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