Reductive (3 + 2) Annulation of Benzils with Pyrylium Salts: Stereoselective Access to Furyl Analogues of cis-Chalcones

Pengwei Tan; Sunewang R. Wang

doi:10.1021/acs.orglett.9b02182

Reductive (3 + 2) Annulation of Benzils with Pyrylium Salts: Stereoselective Access to Furyl Analogues of cis-Chalcones

Pengwei Tan, Sunewang R. Wang

School of Chemistry and Molecular Engineering

East China Normal University

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

34 Scopus citations

Abstract

An unprecedented reductive (3 + 2) annulation of both symmetrical and unsymmetrical benzils with pyrylium salts mediated by P(NMe₂)₃ is described, leading to facile and stereoselective access to the challenging cis-chalcones decorated by various substituted furyl rings under mild conditions. Rather than the extensively studied C1 synthons, the Kukhtin-Ramirez adducts derived from benzils serve as the underexplored C3 synthons in this (3 + 2) annulation with the 2,3-double bond of the 2,6-disubstituted pyrylium ions.

Original language	English
Pages (from-to)	6029-6033
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.9b02182
State	Published - 2 Aug 2019

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title = "Reductive (3 + 2) Annulation of Benzils with Pyrylium Salts: Stereoselective Access to Furyl Analogues of cis-Chalcones",

abstract = "An unprecedented reductive (3 + 2) annulation of both symmetrical and unsymmetrical benzils with pyrylium salts mediated by P(NMe2)3 is described, leading to facile and stereoselective access to the challenging cis-chalcones decorated by various substituted furyl rings under mild conditions. Rather than the extensively studied C1 synthons, the Kukhtin-Ramirez adducts derived from benzils serve as the underexplored C3 synthons in this (3 + 2) annulation with the 2,3-double bond of the 2,6-disubstituted pyrylium ions.",

author = "Pengwei Tan and Wang, \{Sunewang R.\}",

note = "Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = aug,

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doi = "10.1021/acs.orglett.9b02182",

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T1 - Reductive (3 + 2) Annulation of Benzils with Pyrylium Salts

T2 - Stereoselective Access to Furyl Analogues of cis-Chalcones

AU - Tan, Pengwei

AU - Wang, Sunewang R.

PY - 2019/8/2

Y1 - 2019/8/2

N2 - An unprecedented reductive (3 + 2) annulation of both symmetrical and unsymmetrical benzils with pyrylium salts mediated by P(NMe2)3 is described, leading to facile and stereoselective access to the challenging cis-chalcones decorated by various substituted furyl rings under mild conditions. Rather than the extensively studied C1 synthons, the Kukhtin-Ramirez adducts derived from benzils serve as the underexplored C3 synthons in this (3 + 2) annulation with the 2,3-double bond of the 2,6-disubstituted pyrylium ions.

AB - An unprecedented reductive (3 + 2) annulation of both symmetrical and unsymmetrical benzils with pyrylium salts mediated by P(NMe2)3 is described, leading to facile and stereoselective access to the challenging cis-chalcones decorated by various substituted furyl rings under mild conditions. Rather than the extensively studied C1 synthons, the Kukhtin-Ramirez adducts derived from benzils serve as the underexplored C3 synthons in this (3 + 2) annulation with the 2,3-double bond of the 2,6-disubstituted pyrylium ions.

UR - https://www.scopus.com/pages/publications/85070876792

U2 - 10.1021/acs.orglett.9b02182

DO - 10.1021/acs.orglett.9b02182

M3 - 文章

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AN - SCOPUS:85070876792

SN - 1523-7060

VL - 21

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JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Reductive (3 + 2) Annulation of Benzils with Pyrylium Salts: Stereoselective Access to Furyl Analogues of cis-Chalcones

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