Solid-phase synthesis of α-hydroxy phosphonates and hydroxystatine amides. Transition-state isosteres derived from resin-bound amino acid aldehydes

Roland E. Dolle; Timothy F. Herpin; Yvonne Class Shimshock

doi:10.1016/S0040-4039(01)00097-1

Solid-phase synthesis of α-hydroxy phosphonates and hydroxystatine amides. Transition-state isosteres derived from resin-bound amino acid aldehydes

Roland E. Dolle, Timothy F. Herpin, Yvonne Class Shimshock

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29 Scopus citations

Abstract

Resin-bound N-acylated amino acid aldehydes iv were converted in a single step to α-hydroxy phosphonates vii (Pudovik reaction) and in six-steps to hydroxystatine amides viii, demonstrating the utility of intermediates iv for constructing multiple aspartic acid transition-state isosteres.

Original language	English
Pages (from-to)	1855-1858
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4039(01)00097-1
State	Published - Mar 4 2001

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title = "Solid-phase synthesis of α-hydroxy phosphonates and hydroxystatine amides. Transition-state isosteres derived from resin-bound amino acid aldehydes",

abstract = "Resin-bound N-acylated amino acid aldehydes iv were converted in a single step to α-hydroxy phosphonates vii (Pudovik reaction) and in six-steps to hydroxystatine amides viii, demonstrating the utility of intermediates iv for constructing multiple aspartic acid transition-state isosteres.",

author = "Dolle, {Roland E.} and Herpin, {Timothy F.} and Shimshock, {Yvonne Class}",

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T1 - Solid-phase synthesis of α-hydroxy phosphonates and hydroxystatine amides. Transition-state isosteres derived from resin-bound amino acid aldehydes

AU - Dolle, Roland E.

AU - Herpin, Timothy F.

AU - Shimshock, Yvonne Class

PY - 2001/3/4

Y1 - 2001/3/4

N2 - Resin-bound N-acylated amino acid aldehydes iv were converted in a single step to α-hydroxy phosphonates vii (Pudovik reaction) and in six-steps to hydroxystatine amides viii, demonstrating the utility of intermediates iv for constructing multiple aspartic acid transition-state isosteres.

AB - Resin-bound N-acylated amino acid aldehydes iv were converted in a single step to α-hydroxy phosphonates vii (Pudovik reaction) and in six-steps to hydroxystatine amides viii, demonstrating the utility of intermediates iv for constructing multiple aspartic acid transition-state isosteres.

UR - http://www.scopus.com/inward/record.url?scp=0035804454&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)00097-1

DO - 10.1016/S0040-4039(01)00097-1

M3 - Article

AN - SCOPUS:0035804454

SN - 0040-4039

VL - 42

SP - 1855

EP - 1858

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

Solid-phase synthesis of α-hydroxy phosphonates and hydroxystatine amides. Transition-state isosteres derived from resin-bound amino acid aldehydes

Abstract

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