Short, highly efficient syntheses of protected 3-azido- and 4-azidoproline and their precursors

José A. Gómez-Vidal; Richard B. Silverman

doi:10.1021/ol0161054

Short, highly efficient syntheses of protected 3-azido- and 4-azidoproline and their precursors

José A. Gómez-Vidal, Richard B. Silverman^*

^*Corresponding author for this work

Chemistry

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

63 Scopus citations

Abstract

matrix presented An improved synthesis of protected cis- and trans-3-azido-L-proline and cis- and frans-4-azido-L- and -D-proline is reported. These compounds have been synthesized from the corresponding hydroxyproline precursors using diphenylphosphoryl azide under Mitsunobu conditions. Short, highly efficient syntheses of these precursors are described, based on a new lactone-opening reaction and p-nitrobenzoate hydrolysis under very mild conditions.

Original language	English (US)
Pages (from-to)	2481-2484
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	16
DOIs	https://doi.org/10.1021/ol0161054
State	Published - Aug 9 2001

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "matrix presented An improved synthesis of protected cis- and trans-3-azido-L-proline and cis- and frans-4-azido-L- and -D-proline is reported. These compounds have been synthesized from the corresponding hydroxyproline precursors using diphenylphosphoryl azide under Mitsunobu conditions. Short, highly efficient syntheses of these precursors are described, based on a new lactone-opening reaction and p-nitrobenzoate hydrolysis under very mild conditions.",

author = "G{\'o}mez-Vidal, {Jos{\'e} A.} and Silverman, {Richard B.}",

year = "2001",

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journal = "Organic Letters",

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T1 - Short, highly efficient syntheses of protected 3-azido- and 4-azidoproline and their precursors

AU - Gómez-Vidal, José A.

AU - Silverman, Richard B.

PY - 2001/8/9

Y1 - 2001/8/9

N2 - matrix presented An improved synthesis of protected cis- and trans-3-azido-L-proline and cis- and frans-4-azido-L- and -D-proline is reported. These compounds have been synthesized from the corresponding hydroxyproline precursors using diphenylphosphoryl azide under Mitsunobu conditions. Short, highly efficient syntheses of these precursors are described, based on a new lactone-opening reaction and p-nitrobenzoate hydrolysis under very mild conditions.

AB - matrix presented An improved synthesis of protected cis- and trans-3-azido-L-proline and cis- and frans-4-azido-L- and -D-proline is reported. These compounds have been synthesized from the corresponding hydroxyproline precursors using diphenylphosphoryl azide under Mitsunobu conditions. Short, highly efficient syntheses of these precursors are described, based on a new lactone-opening reaction and p-nitrobenzoate hydrolysis under very mild conditions.

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JF - Organic Letters

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Short, highly efficient syntheses of protected 3-azido- and 4-azidoproline and their precursors

Abstract

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