Proline-promoted dehydroxylation of α-ketols

Yelena Mostinski; David Lankri; Yana Konovalov; Riva Nataf; Dmitry Tsvelikhovsky

doi:10.1039/c9sc02543j

Proline-promoted dehydroxylation of α-ketols

Yelena Mostinski
, David Lankri
, Yana Konovalov
, Riva Nataf
, Dmitry Tsvelikhovsky^*

^*Corresponding author for this work

School of Pharmacy

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

4 Scopus citations

Abstract

A new single-step proline-potassium acetate promoted reductive dehydroxylation of α-ketols is reported. We introduce the unexplored reactivity of proline and, for the first time, reveal its ability to function as a reducing agent. The developed metal-free and open-flask operation generally results in good yields. Our protocol allows the challenging selective dehydroxylation of hydroxyketones without affecting other functional groups.

Original language	English
Pages (from-to)	9345-9350
Number of pages	6
Journal	Chemical Science
Volume	10
Issue number	40
DOIs	https://doi.org/10.1039/c9sc02543j
State	Published - 2019

Bibliographical note

Funding Information:
This project was nancially supported by Yissum Research Development Company of the Hebrew University of Jerusalem. We thank Dr Aviva Friedman-Ezra for NMR assistance.

Publisher Copyright:
This journal is © The Royal Society of Chemistry.

Access to Document

10.1039/c9sc02543j

Cite this

@article{12af29ee15df409d8f47893bd885e2d7,

title = "Proline-promoted dehydroxylation of α-ketols",

abstract = "A new single-step proline-potassium acetate promoted reductive dehydroxylation of α-ketols is reported. We introduce the unexplored reactivity of proline and, for the first time, reveal its ability to function as a reducing agent. The developed metal-free and open-flask operation generally results in good yields. Our protocol allows the challenging selective dehydroxylation of hydroxyketones without affecting other functional groups.",

author = "Yelena Mostinski and David Lankri and Yana Konovalov and Riva Nataf and Dmitry Tsvelikhovsky",

note = "Publisher Copyright: This journal is {\textcopyright} The Royal Society of Chemistry.",

year = "2019",

doi = "10.1039/c9sc02543j",

language = "אנגלית",

volume = "10",

pages = "9345--9350",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "40",

}

TY - JOUR

T1 - Proline-promoted dehydroxylation of α-ketols

AU - Mostinski, Yelena

AU - Lankri, David

AU - Konovalov, Yana

AU - Nataf, Riva

AU - Tsvelikhovsky, Dmitry

PY - 2019

Y1 - 2019

N2 - A new single-step proline-potassium acetate promoted reductive dehydroxylation of α-ketols is reported. We introduce the unexplored reactivity of proline and, for the first time, reveal its ability to function as a reducing agent. The developed metal-free and open-flask operation generally results in good yields. Our protocol allows the challenging selective dehydroxylation of hydroxyketones without affecting other functional groups.

AB - A new single-step proline-potassium acetate promoted reductive dehydroxylation of α-ketols is reported. We introduce the unexplored reactivity of proline and, for the first time, reveal its ability to function as a reducing agent. The developed metal-free and open-flask operation generally results in good yields. Our protocol allows the challenging selective dehydroxylation of hydroxyketones without affecting other functional groups.

UR - https://www.scopus.com/pages/publications/85073552892

U2 - 10.1039/c9sc02543j

DO - 10.1039/c9sc02543j

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:85073552892

SN - 2041-6520

VL - 10

SP - 9345

EP - 9350

JO - Chemical Science

JF - Chemical Science

IS - 40

ER -

Proline-promoted dehydroxylation of α-ketols

Abstract

Bibliographical note

Access to Document

Other files and links

Fingerprint

Cite this