Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates

Jun Sun; Fangcheng He; Zhongyao Wang; Dingwu Pan; Pengcheng Zheng; Chengli Mou; Zhichao Jin; Yonggui Robin Chi

doi:10.1039/c8cc03017k

Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates

Jun Sun, Fangcheng He, Zhongyao Wang, Dingwu Pan, Pengcheng Zheng, Chengli Mou, Zhichao Jin^*, Yonggui Robin Chi

^*Corresponding author for this work

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

19 Citations (Scopus)

Abstract

A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between α,β-unsaturated aldehydes and α-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities. Preliminary studies show that the products from our reactions exhibit anti-bacterial (X. oryzae pv. oryzae) and anti-viral (Tobacco Mosaic Virus) activities for potential use in plant protection.

Original language	English
Pages (from-to)	6040-6043
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	47
DOIs	https://doi.org/10.1039/c8cc03017k
Publication status	Published - 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2018 The Royal Society of Chemistry.

ASJC Scopus Subject Areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/c8cc03017k

Cite this

@article{3fd87fc420ad488f897f700ba04815ac,

title = "Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates",

abstract = "A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between α,β-unsaturated aldehydes and α-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities. Preliminary studies show that the products from our reactions exhibit anti-bacterial (X. oryzae pv. oryzae) and anti-viral (Tobacco Mosaic Virus) activities for potential use in plant protection.",

author = "Jun Sun and Fangcheng He and Zhongyao Wang and Dingwu Pan and Pengcheng Zheng and Chengli Mou and Zhichao Jin and Chi, {Yonggui Robin}",

note = "Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8cc03017k",

language = "English",

volume = "54",

pages = "6040--6043",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "47",

}

TY - JOUR

T1 - Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates

AU - Sun, Jun

AU - He, Fangcheng

AU - Wang, Zhongyao

AU - Pan, Dingwu

AU - Zheng, Pengcheng

AU - Mou, Chengli

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2018

Y1 - 2018

N2 - A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between α,β-unsaturated aldehydes and α-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities. Preliminary studies show that the products from our reactions exhibit anti-bacterial (X. oryzae pv. oryzae) and anti-viral (Tobacco Mosaic Virus) activities for potential use in plant protection.

AB - A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between α,β-unsaturated aldehydes and α-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities. Preliminary studies show that the products from our reactions exhibit anti-bacterial (X. oryzae pv. oryzae) and anti-viral (Tobacco Mosaic Virus) activities for potential use in plant protection.

UR - http://www.scopus.com/inward/record.url?scp=85048367118&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85048367118&partnerID=8YFLogxK

U2 - 10.1039/c8cc03017k

DO - 10.1039/c8cc03017k

M3 - Article

C2 - 29799045

AN - SCOPUS:85048367118

SN - 1359-7345

VL - 54

SP - 6040

EP - 6043

JO - Chemical Communications

JF - Chemical Communications

IS - 47

ER -

Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this