Allylic hydroxy phosphonates: Versatile chiral building blocks

Antonette De La Cruz; Anyu He; Anchalee Thanavaro; Bingli Yan; Christopher D. Spilling; Nigam P. Rath

doi:10.1016/j.jorganchem.2004.11.019

Allylic hydroxy phosphonates: Versatile chiral building blocks

Antonette De La Cruz
, Anyu He
, Anchalee Thanavaro
, Bingli Yan
, Christopher D. Spilling
, Nigam P. Rath

Department of Chemistry

Research output: Contribution to journal › Conference article › peer-review

24 Scopus citations

Abstract

Allylic hydroxy phosphonates are converted into β and γ substituted amino phosphonates using a series of palladium-catalyzed reactions. The judicious selection of nitrogen nucleophile and palladium catalyst allow for excellent regio- and stereochemical control. Palladium(0)-catalyzed amine addition or tosyl carbamate rearrangement gives rise to the γ-substituted phosphonates, whereas, reaction of tosyl carbamates with palladium (II) and base gives oxazolidinones (β-substitution).

Original language	English
Pages (from-to)	2577-2592
Number of pages	16
Journal	Journal of Organometallic Chemistry
Volume	690
Issue number	10
DOIs	https://doi.org/10.1016/j.jorganchem.2004.11.019
State	Published - May 16 2005
Event	16th International Conference on Phosphorus Chemistry ICPC - Duration: Jul 4 2004 → Jul 9 2004

Keywords

Hydroy phosphonate

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10.1016/j.jorganchem.2004.11.019

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@article{86824a60b95743c885cd5c669b32982d,

title = "Allylic hydroxy phosphonates: Versatile chiral building blocks",

abstract = "Allylic hydroxy phosphonates are converted into β and γ substituted amino phosphonates using a series of palladium-catalyzed reactions. The judicious selection of nitrogen nucleophile and palladium catalyst allow for excellent regio- and stereochemical control. Palladium(0)-catalyzed amine addition or tosyl carbamate rearrangement gives rise to the γ-substituted phosphonates, whereas, reaction of tosyl carbamates with palladium (II) and base gives oxazolidinones (β-substitution).",

keywords = "Hydroy phosphonate",

author = "\{De La Cruz\}, Antonette and Anyu He and Anchalee Thanavaro and Bingli Yan and Spilling, \{Christopher D.\} and Rath, \{Nigam P.\}",

year = "2005",

month = may,

day = "16",

doi = "10.1016/j.jorganchem.2004.11.019",

language = "English",

volume = "690",

pages = "2577--2592",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

number = "10",

note = "16th International Conference on Phosphorus Chemistry ICPC ; Conference date: 04-07-2004 Through 09-07-2004",

}

TY - JOUR

T1 - Allylic hydroxy phosphonates

T2 - 16th International Conference on Phosphorus Chemistry ICPC

AU - De La Cruz, Antonette

AU - He, Anyu

AU - Thanavaro, Anchalee

AU - Yan, Bingli

AU - Spilling, Christopher D.

AU - Rath, Nigam P.

PY - 2005/5/16

Y1 - 2005/5/16

N2 - Allylic hydroxy phosphonates are converted into β and γ substituted amino phosphonates using a series of palladium-catalyzed reactions. The judicious selection of nitrogen nucleophile and palladium catalyst allow for excellent regio- and stereochemical control. Palladium(0)-catalyzed amine addition or tosyl carbamate rearrangement gives rise to the γ-substituted phosphonates, whereas, reaction of tosyl carbamates with palladium (II) and base gives oxazolidinones (β-substitution).

AB - Allylic hydroxy phosphonates are converted into β and γ substituted amino phosphonates using a series of palladium-catalyzed reactions. The judicious selection of nitrogen nucleophile and palladium catalyst allow for excellent regio- and stereochemical control. Palladium(0)-catalyzed amine addition or tosyl carbamate rearrangement gives rise to the γ-substituted phosphonates, whereas, reaction of tosyl carbamates with palladium (II) and base gives oxazolidinones (β-substitution).

KW - Hydroy phosphonate

UR - https://www.scopus.com/pages/publications/17944373472

U2 - 10.1016/j.jorganchem.2004.11.019

DO - 10.1016/j.jorganchem.2004.11.019

M3 - Conference article

AN - SCOPUS:17944373472

SN - 0022-328X

VL - 690

SP - 2577

EP - 2592

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 10

Y2 - 4 July 2004 through 9 July 2004

ER -

Allylic hydroxy phosphonates: Versatile chiral building blocks

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Keywords

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