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

Published on Nov 7, 2019in Chemical Communications6.164
· DOI :10.1039/C9CC07477E
Mukulesh Mondal1
Estimated H-index: 1
(Oakland University),
Mukulesh Mondal8
Estimated H-index: 8
(Oakland University)
+ 2 AuthorsNessan J. Kerrigan12
Estimated H-index: 12
(DCU: Dublin City University)
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).
  • References (56)
  • Citations (1)
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References56
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#1Mukulesh Mondal (Oakland University)H-Index: 8
#1Mukulesh Mondal (Oakland University)H-Index: 1
Last. Nessan J. Kerrigan (DCU: Dublin City University)H-Index: 1
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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 product...
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#1Satavisha Kayal (Tohoku University)H-Index: 1
#2Jun Kikuchi (Tohoku University)H-Index: 7
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An enantioselective formal α-vinylation of ketones for the construction of an all-carbon quaternary center was established using the vinylogous Wagner–Meerwein shift through the activation of the leaving group by a chiral phosphoramide as the chiral Bronsted acid catalyst. The present reaction afforded enantioenriched all-carbon quaternary α-vinyl ketones in high yields with high enantioselectivities in most cases. Experimental elucidation of the reaction mechanism suggested that the discriminat...
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#1Wei Liu (CAS: Chinese Academy of Sciences)H-Index: 1
#2Subramani Rajkumar (ShanghaiTech University)H-Index: 3
Last. Xiaoyu Yang (ShanghaiTech University)H-Index: 9
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The asymmetric Friedel–Crafts alkylation reactions of indoles with β-substituted cyclopentenimines enabled by chiral phosphoric acid catalysis has been developed, which affords adducts possessing an all-carbon stereocenter with high levels of enantioselectivities. Furthermore, the addition products could be readily converted into two types of useful but previously challenging chiral building blocks, such as β-alkyl-β-indolyl cyclopentanones and β-alkyl-β-indolyl cyclopentylamides, in one pot via...
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#1Zhiwei Chen (UCI: University of California, Irvine)H-Index: 7
#2Yusuke Aota (Kyoto University)H-Index: 1
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: We report a dynamic kinetic resolution (DKR) of chiral 4-pentenals by olefin hydroacylation. A primary amine racemizes the aldehyde substrate via enamine formation and hydrolysis. Then, a cationic rhodium catalyst promotes hydroacylation to generate α,γ-disubstituted cyclopentanones with high enantio- and diastereoselectivities.
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A novel sequential reaction that combines a visible light-induced Wolff rearrangement of α-diazoketones and a Pd-catalyzed [3+2] cycloaddition of vinyl cyclopropanes with the resulting ketenes is described in this work. Selective O-allylic alkylation was observed over C-allylic alkylation, which unexpectedly led to a series of highly functionalized tetrahydrofurans with high efficiency (20 examples, 58–99% yields).
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#1André U. Augustin (Braunschweig University of Technology)H-Index: 6
#2Marius Busse (Braunschweig University of Technology)H-Index: 1
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Donor–acceptor cyclopropanes were reacted under Lewis acid catalysis with 3-thioxocyclobutanones as surrogates for disubstituted thioketenes. A broad scope of 2-substituted tetrahydrothiophenes with a semicyclic double bond was obtained under mild conditions with high functional group tolerance and in excellent yield. A sequence of a formal [3 + 2]-cycloaddition followed by the subsequent release of disubstituted ketene is postulated as the mechanism.
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#1Kamal Verma (IIT-RPR: Indian Institute of Technology Ropar)H-Index: 3
#2Prabal Banerjee (IIT-RPR: Indian Institute of Technology Ropar)H-Index: 13
Lewis acid catalyzed formal [3+2] cycloadditions of 1-azadienes with donor acceptor cyclopropanes to synthesize varieties of imine functionalized cyclopentanes and pyrrolidine derivatives in moderate to high yield have been developed. Moreover, pharmaceutically relevant azabicyclo[3.2.1]octane, bearing two all-carbon quaternary stereogenic centers at the bridgehead positions, has been synthesized by nosyl group deprotection and intramolecular amidation of imine functionalized cyclopentane deriva...
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#1Xiang-Yu Chen (RWTH Aachen University)H-Index: 8
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A novel short entry to 3,4-disubstituted adipic acids has been developed by employing an asymmetric NHC-catalyzed [3+2] cycloaddition of enals with masked cinnammates in good yields and high stereoselectivities. The synthetic utility of the protocol was demonstrated by the basic conversion of the masked cyclopentanone intermediates to 3S,4S-disubstituted adipic acid precursors of pharmaceutically important gababutins.
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Reported herein is a light-triggered organocatalytic strategy for the desymmetrization of achiral 2-fluoro-substituted cyclopentane-1,3-diketones. The chemistry is based on an intermolecular aldol reaction of photochemically generated hydroxy-o-quinodimethanes and simultaneously forges two adjacent fully substituted carbon stereocenters, with one bearing a stereogenic carbon–fluorine unit. The method uses readily available substrates, a simple chiral organocatalyst, and mild reaction conditions ...
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#1Alexander Lücht (Braunschweig University of Technology)H-Index: 4
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