Synthesis of Chiral 2,3-Dihydrofurans via One-Pot Pd-Catalyzed Asymmetric Allylic Cycloaddition and a Retro-Dieckmann Fragmentation Cascade

Babar Hussain Shah; Sardaraz Khan; Can Zhao; Yong Jian Zhang

doi:10.1021/acs.joc.3c00976

Synthesis of Chiral 2,3-Dihydrofurans via One-Pot Pd-Catalyzed Asymmetric Allylic Cycloaddition and a Retro-Dieckmann Fragmentation Cascade

Babar Hussain Shah
, Sardaraz Khan
, Can Zhao
, Yong Jian Zhang^*

^*Corresponding author for this work

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

3 Scopus citations

Abstract

An efficient method for the enantioselective synthesis of 2,3-dihydrofurans bearing a quaternary stereocenter has been developed via Pd-catalyzed asymmetric allylic cycloaddition and a retro-Dieckmann Fragmentation cascade. The asymmetric allylic cycloaddition of vinylethylene carbonates with 3-cyanochromone followed by base-assisted retro-Dieckmann fragmentation proceeded smoothly via a one-pot process to produce chiral 3,4-disubstituted 2,3-dihydrofurans in high yields with excellent enantioselectivities.

Original language	English
Pages (from-to)	12100-12104
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	88
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.3c00976
State	Published - 18 Aug 2023
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society.

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/acs.joc.3c00976

Cite this

@article{2cc9ded911b04868a42242ae9105e4ea,

title = "Synthesis of Chiral 2,3-Dihydrofurans via One-Pot Pd-Catalyzed Asymmetric Allylic Cycloaddition and a Retro-Dieckmann Fragmentation Cascade",

abstract = "An efficient method for the enantioselective synthesis of 2,3-dihydrofurans bearing a quaternary stereocenter has been developed via Pd-catalyzed asymmetric allylic cycloaddition and a retro-Dieckmann Fragmentation cascade. The asymmetric allylic cycloaddition of vinylethylene carbonates with 3-cyanochromone followed by base-assisted retro-Dieckmann fragmentation proceeded smoothly via a one-pot process to produce chiral 3,4-disubstituted 2,3-dihydrofurans in high yields with excellent enantioselectivities.",

author = "Shah, \{Babar Hussain\} and Sardaraz Khan and Can Zhao and Zhang, \{Yong Jian\}",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

month = aug,

day = "18",

doi = "10.1021/acs.joc.3c00976",

language = "English",

volume = "88",

pages = "12100--12104",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "16",

}

TY - JOUR

T1 - Synthesis of Chiral 2,3-Dihydrofurans via One-Pot Pd-Catalyzed Asymmetric Allylic Cycloaddition and a Retro-Dieckmann Fragmentation Cascade

AU - Shah, Babar Hussain

AU - Khan, Sardaraz

AU - Zhao, Can

AU - Zhang, Yong Jian

PY - 2023/8/18

Y1 - 2023/8/18

N2 - An efficient method for the enantioselective synthesis of 2,3-dihydrofurans bearing a quaternary stereocenter has been developed via Pd-catalyzed asymmetric allylic cycloaddition and a retro-Dieckmann Fragmentation cascade. The asymmetric allylic cycloaddition of vinylethylene carbonates with 3-cyanochromone followed by base-assisted retro-Dieckmann fragmentation proceeded smoothly via a one-pot process to produce chiral 3,4-disubstituted 2,3-dihydrofurans in high yields with excellent enantioselectivities.

AB - An efficient method for the enantioselective synthesis of 2,3-dihydrofurans bearing a quaternary stereocenter has been developed via Pd-catalyzed asymmetric allylic cycloaddition and a retro-Dieckmann Fragmentation cascade. The asymmetric allylic cycloaddition of vinylethylene carbonates with 3-cyanochromone followed by base-assisted retro-Dieckmann fragmentation proceeded smoothly via a one-pot process to produce chiral 3,4-disubstituted 2,3-dihydrofurans in high yields with excellent enantioselectivities.

UR - https://www.scopus.com/pages/publications/85168372962

U2 - 10.1021/acs.joc.3c00976

DO - 10.1021/acs.joc.3c00976

M3 - Article

AN - SCOPUS:85168372962

SN - 0022-3263

VL - 88

SP - 12100

EP - 12104

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 16

ER -

Synthesis of Chiral 2,3-Dihydrofurans via One-Pot Pd-Catalyzed Asymmetric Allylic Cycloaddition and a Retro-Dieckmann Fragmentation Cascade

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this