Phosphorylation Organocatalysts Highly Active by Design

Amit Fallek; Mor Weiss-Shtofman; Maria Kramer; Roman Dobrovetsky; Moshe Portnoy

doi:10.1021/acs.orglett.0c01226

Phosphorylation Organocatalysts Highly Active by Design

Amit Fallek, Mor Weiss-Shtofman, Maria Kramer, Roman Dobrovetsky, Moshe Portnoy

School of Chemistry

Tel Aviv University

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

Abstract

The activity of nucleophilic organocatalysts for alcohol/phenol phosphorylation was enhanced through attaching oligoether appendages to a benzyl substituent on imidazole- or aminopyridine-based active units, presumably because of stabilizing n-cation interactions of the ethereal oxygens with the positively charged aza-heterocycle in the catalytic intermediates, and was substantially higher than that of known benchmark catalysts for a range of substrates. Density functional theory calculations and the study of analogues having a lower potential for such stabilizing interactions support our hypothesis.

Original language	English
Pages (from-to)	3722-3727
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.0c01226
State	Published - 1 May 2020

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c01226

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title = "Phosphorylation Organocatalysts Highly Active by Design",

abstract = "The activity of nucleophilic organocatalysts for alcohol/phenol phosphorylation was enhanced through attaching oligoether appendages to a benzyl substituent on imidazole- or aminopyridine-based active units, presumably because of stabilizing n-cation interactions of the ethereal oxygens with the positively charged aza-heterocycle in the catalytic intermediates, and was substantially higher than that of known benchmark catalysts for a range of substrates. Density functional theory calculations and the study of analogues having a lower potential for such stabilizing interactions support our hypothesis.",

author = "Amit Fallek and Mor Weiss-Shtofman and Maria Kramer and Roman Dobrovetsky and Moshe Portnoy",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = may,

day = "1",

doi = "10.1021/acs.orglett.0c01226",

language = "الإنجليزيّة",

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TY - JOUR

T1 - Phosphorylation Organocatalysts Highly Active by Design

AU - Fallek, Amit

AU - Weiss-Shtofman, Mor

AU - Kramer, Maria

AU - Dobrovetsky, Roman

AU - Portnoy, Moshe

PY - 2020/5/1

Y1 - 2020/5/1

N2 - The activity of nucleophilic organocatalysts for alcohol/phenol phosphorylation was enhanced through attaching oligoether appendages to a benzyl substituent on imidazole- or aminopyridine-based active units, presumably because of stabilizing n-cation interactions of the ethereal oxygens with the positively charged aza-heterocycle in the catalytic intermediates, and was substantially higher than that of known benchmark catalysts for a range of substrates. Density functional theory calculations and the study of analogues having a lower potential for such stabilizing interactions support our hypothesis.

AB - The activity of nucleophilic organocatalysts for alcohol/phenol phosphorylation was enhanced through attaching oligoether appendages to a benzyl substituent on imidazole- or aminopyridine-based active units, presumably because of stabilizing n-cation interactions of the ethereal oxygens with the positively charged aza-heterocycle in the catalytic intermediates, and was substantially higher than that of known benchmark catalysts for a range of substrates. Density functional theory calculations and the study of analogues having a lower potential for such stabilizing interactions support our hypothesis.

UR - http://www.scopus.com/inward/record.url?scp=85083880626&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c01226

DO - 10.1021/acs.orglett.0c01226

M3 - مقالة

C2 - 32319783

SN - 1523-7060

VL - 22

SP - 3722

EP - 3727

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Phosphorylation Organocatalysts Highly Active by Design

Abstract

All Science Journal Classification (ASJC) codes

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