Asymmetric synthesis of cyclopentanones through dual Lewis acid-catalysed [3+2]-cycloaddition of donor-Acceptor cyclopropanes with ketenes

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

*Kontaktforfatter for dette arbejde

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

When InBr3-EtAlCl2 (15-30 mol%) was used as a dual Lewis acid system to promote the formal [3+2]-cycloaddition of enantioenriched donor-Acceptor cyclopropanes with ketenes, cyclopentanones were formed in good to excellent yields (84-99%, 18 examples), and with excellent transfer of chirality (15 examples, 90% ee to >99% ee).

OriginalsprogEngelsk
TidsskriftChemical Communications
Vol/bind55
Udgave nummer90
Sider (fra-til)13558-13561
Antal sider4
ISSN1359-7345
DOI
StatusUdgivet - 2019

Fingeraftryk

Cyclopropanes
Lewis Acids
Cycloaddition
Chirality
Acids
dichloroethylaluminum
indium bromide
cyclopentanone

Citer dette

Mondal, Mukulesh ; Panda, Manashi ; Davis, Nicholas W. ; McKee, Vickie ; Kerrigan, Nessan J. / Asymmetric synthesis of cyclopentanones through dual Lewis acid-catalysed [3+2]-cycloaddition of donor-Acceptor cyclopropanes with ketenes. I: Chemical Communications. 2019 ; Bind 55, Nr. 90. s. 13558-13561.
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title = "Asymmetric synthesis of cyclopentanones through dual Lewis acid-catalysed [3+2]-cycloaddition of donor-Acceptor cyclopropanes with ketenes",
abstract = "When InBr3-EtAlCl2 (15-30 mol{\%}) was used as a dual Lewis acid system to promote the formal [3+2]-cycloaddition of enantioenriched donor-Acceptor cyclopropanes with ketenes, cyclopentanones were formed in good to excellent yields (84-99{\%}, 18 examples), and with excellent transfer of chirality (15 examples, 90{\%} ee to >99{\%} ee).",
author = "Mukulesh Mondal and Manashi Panda and Davis, {Nicholas W.} and Vickie McKee and Kerrigan, {Nessan J.}",
year = "2019",
doi = "10.1039/c9cc07477e",
language = "English",
volume = "55",
pages = "13558--13561",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
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Asymmetric synthesis of cyclopentanones through dual Lewis acid-catalysed [3+2]-cycloaddition of donor-Acceptor cyclopropanes with ketenes. / Mondal, Mukulesh; Panda, Manashi; Davis, Nicholas W.; McKee, Vickie; Kerrigan, Nessan J.

I: Chemical Communications, Bind 55, Nr. 90, 2019, s. 13558-13561.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Asymmetric synthesis of cyclopentanones through dual Lewis acid-catalysed [3+2]-cycloaddition of donor-Acceptor cyclopropanes with ketenes

AU - Mondal, Mukulesh

AU - Panda, Manashi

AU - Davis, Nicholas W.

AU - McKee, Vickie

AU - Kerrigan, Nessan J.

PY - 2019

Y1 - 2019

N2 - When InBr3-EtAlCl2 (15-30 mol%) was used as a dual Lewis acid system to promote the formal [3+2]-cycloaddition of enantioenriched donor-Acceptor cyclopropanes with ketenes, cyclopentanones were formed in good to excellent yields (84-99%, 18 examples), and with excellent transfer of chirality (15 examples, 90% ee to >99% ee).

AB - When InBr3-EtAlCl2 (15-30 mol%) was used as a dual Lewis acid system to promote the formal [3+2]-cycloaddition of enantioenriched donor-Acceptor cyclopropanes with ketenes, cyclopentanones were formed in good to excellent yields (84-99%, 18 examples), and with excellent transfer of chirality (15 examples, 90% ee to >99% ee).

U2 - 10.1039/c9cc07477e

DO - 10.1039/c9cc07477e

M3 - Journal article

VL - 55

SP - 13558

EP - 13561

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 90

ER -