Asymmetric synthesis of α-hydroxy- phosphonamides, phosphonates and phosphonic acids

Vincent J. Blazis; Kevin J. Koeller; Christopher Spilling

doi:10.1016/0957-4166(94)80002-2

Asymmetric synthesis of α-hydroxy- phosphonamides, phosphonates and phosphonic acids

Vincent J. Blazis, Kevin J. Koeller, Christopher Spilling

University of Missouri-St. Louis

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

Abstract

 The addition of the anion of the bicyclic chiral phosphorous acid diamide 1a to aldehydes in THF solution gave α-hydroxy phosphonamides in good yield and good diastereoselectivity (54–93% de). The phosphonamides were hydrolyzed with aqueous HCl in dioxane to give α-hydroxy phosphonic acids. Methylation of the resulting phosphonic acids with diazomethane gave α-hydroxy dimethyl phosphonates without loss of stereochemical integrety.
 
 The addition of the chiral phosphorous acid diamide (1a) to aldehydes gave 1-hydroxy phosphonamides in good yield and with good diastereoselectivity (54–93% de). Hydrolysis of the phosphonamides gave the phosphonic acids, which were methylated to yield the dimethyl phosphonates.

Original language	American English
Journal	Tetrahedron: Asymmetry
Volume	5
DOIs	https://doi.org/10.1016/0957-4166(94)80002-2
State	Published - Apr 1994

Disciplines

Physical Sciences and Mathematics
Chemistry
Organic Chemistry

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title = "Asymmetric synthesis of α-hydroxy- phosphonamides, phosphonates and phosphonic acids",

abstract = " The addition of the anion of the bicyclic chiral phosphorous acid diamide 1a to aldehydes in THF solution gave α-hydroxy phosphonamides in good yield and good diastereoselectivity (54–93% de). The phosphonamides were hydrolyzed with aqueous HCl in dioxane to give α-hydroxy phosphonic acids. Methylation of the resulting phosphonic acids with diazomethane gave α-hydroxy dimethyl phosphonates without loss of stereochemical integrety. The addition of the chiral phosphorous acid diamide (1a) to aldehydes gave 1-hydroxy phosphonamides in good yield and with good diastereoselectivity (54–93% de). Hydrolysis of the phosphonamides gave the phosphonic acids, which were methylated to yield the dimethyl phosphonates.",

author = "Blazis, {Vincent J.} and Koeller, {Kevin J.} and Christopher Spilling",

note = "The addition of the anion of the bicyclic chiral phosphorous acid diamide 1a to aldehydes in THF solution gave α-hydroxy phosphonamides in good yield and good diastereoselectivity (54-93% de). The phosphonamides were hydrolyzed with aqueous HCl in dioxane to give α-hydroxy phosphonic acids.",

year = "1994",

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doi = "10.1016/0957-4166(94)80002-2",

language = "American English",

volume = "5",

journal = "Tetrahedron: Asymmetry",

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TY - JOUR

T1 - Asymmetric synthesis of α-hydroxy- phosphonamides, phosphonates and phosphonic acids

AU - Blazis, Vincent J.

AU - Koeller, Kevin J.

AU - Spilling, Christopher

N1 - The addition of the anion of the bicyclic chiral phosphorous acid diamide 1a to aldehydes in THF solution gave α-hydroxy phosphonamides in good yield and good diastereoselectivity (54-93% de). The phosphonamides were hydrolyzed with aqueous HCl in dioxane to give α-hydroxy phosphonic acids.

PY - 1994/4

Y1 - 1994/4

N2 - The addition of the anion of the bicyclic chiral phosphorous acid diamide 1a to aldehydes in THF solution gave α-hydroxy phosphonamides in good yield and good diastereoselectivity (54–93% de). The phosphonamides were hydrolyzed with aqueous HCl in dioxane to give α-hydroxy phosphonic acids. Methylation of the resulting phosphonic acids with diazomethane gave α-hydroxy dimethyl phosphonates without loss of stereochemical integrety. The addition of the chiral phosphorous acid diamide (1a) to aldehydes gave 1-hydroxy phosphonamides in good yield and with good diastereoselectivity (54–93% de). Hydrolysis of the phosphonamides gave the phosphonic acids, which were methylated to yield the dimethyl phosphonates.

AB - The addition of the anion of the bicyclic chiral phosphorous acid diamide 1a to aldehydes in THF solution gave α-hydroxy phosphonamides in good yield and good diastereoselectivity (54–93% de). The phosphonamides were hydrolyzed with aqueous HCl in dioxane to give α-hydroxy phosphonic acids. Methylation of the resulting phosphonic acids with diazomethane gave α-hydroxy dimethyl phosphonates without loss of stereochemical integrety. The addition of the chiral phosphorous acid diamide (1a) to aldehydes gave 1-hydroxy phosphonamides in good yield and with good diastereoselectivity (54–93% de). Hydrolysis of the phosphonamides gave the phosphonic acids, which were methylated to yield the dimethyl phosphonates.

UR - https://www.sciencedirect.com/science/article/abs/pii/0957416694800022

U2 - 10.1016/0957-4166(94)80002-2

DO - 10.1016/0957-4166(94)80002-2

M3 - Article

VL - 5

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

ER -

Asymmetric synthesis of α-hydroxy- phosphonamides, phosphonates and phosphonic acids

Abstract

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