Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes

Mukulesh Mondal, Manashi Panda, Vickie McKee, Nessan J. Kerrigan*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

In this article we describe a new asymmetric synthesis of highly substituted tetrahydrofurans through a Pd(PPh3)4-catalyzed formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes and ketenes. The desired structural motif was formed in moderate to excellent yields (42-84% for 16 examples), with excellent Z:E isomer diastereoselectivity (≥19:1 for 16 examples), and with good to excellent enantioselectivity in all cases examined (83-97% ee for 6 examples). The synthetic utility of the products was illustrated by a number of diastereoselective transformations into reduced tetrahydrofurans and spirocyclic tetrahydrofuran-barbiturate derivatives. ©

Original languageEnglish
JournalJournal of Organic Chemistry
Volume84
Issue number18
Pages (from-to)11983-11991
Number of pages9
ISSN0022-3263
DOIs
Publication statusPublished - 20. Sep 2019

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Furans
Cycloaddition
Palladium
Cyclopropanes
Enantioselectivity
Isomers
Derivatives
tetrahydrofuran
barbituric acid

Cite this

@article{b45d88de5208426c8080ee73db095970,
title = "Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes",
abstract = "In this article we describe a new asymmetric synthesis of highly substituted tetrahydrofurans through a Pd(PPh3)4-catalyzed formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes and ketenes. The desired structural motif was formed in moderate to excellent yields (42-84{\%} for 16 examples), with excellent Z:E isomer diastereoselectivity (≥19:1 for 16 examples), and with good to excellent enantioselectivity in all cases examined (83-97{\%} ee for 6 examples). The synthetic utility of the products was illustrated by a number of diastereoselective transformations into reduced tetrahydrofurans and spirocyclic tetrahydrofuran-barbiturate derivatives. {\circledC}",
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language = "English",
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Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes. / Mondal, Mukulesh; Panda, Manashi; McKee, Vickie; Kerrigan, Nessan J.

In: Journal of Organic Chemistry, Vol. 84, No. 18, 20.09.2019, p. 11983-11991.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes

AU - Mondal, Mukulesh

AU - Panda, Manashi

AU - McKee, Vickie

AU - Kerrigan, Nessan J.

PY - 2019/9/20

Y1 - 2019/9/20

N2 - In this article we describe a new asymmetric synthesis of highly substituted tetrahydrofurans through a Pd(PPh3)4-catalyzed formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes and ketenes. The desired structural motif was formed in moderate to excellent yields (42-84% for 16 examples), with excellent Z:E isomer diastereoselectivity (≥19:1 for 16 examples), and with good to excellent enantioselectivity in all cases examined (83-97% ee for 6 examples). The synthetic utility of the products was illustrated by a number of diastereoselective transformations into reduced tetrahydrofurans and spirocyclic tetrahydrofuran-barbiturate derivatives. ©

AB - In this article we describe a new asymmetric synthesis of highly substituted tetrahydrofurans through a Pd(PPh3)4-catalyzed formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes and ketenes. The desired structural motif was formed in moderate to excellent yields (42-84% for 16 examples), with excellent Z:E isomer diastereoselectivity (≥19:1 for 16 examples), and with good to excellent enantioselectivity in all cases examined (83-97% ee for 6 examples). The synthetic utility of the products was illustrated by a number of diastereoselective transformations into reduced tetrahydrofurans and spirocyclic tetrahydrofuran-barbiturate derivatives. ©

U2 - 10.1021/acs.joc.9b01854

DO - 10.1021/acs.joc.9b01854

M3 - Journal article

VL - 84

SP - 11983

EP - 11991

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 18

ER -