An enantioselective synthesis of 3,4-disubstituted butyrolactones

Honda, Toshio; Kimura, Nobuaki

doi:10.1039/c39940000077

Cited by 50 publications

(13 citation statements)

References 4 publications

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“…A number of methods have been developed to access enantiomerically enriched cyclobutane scaffolds, including [2+2] cycloaddition, rearrangement, and other transformations . However, the enantioselective desymmetrization of readily available cyclobutanones has received less attention …”

Section: Figurementioning

confidence: 99%

Enantioselective Desymmetrization of Cyclobutanones Enabled by Synergistic Palladium/Enamine Catalysis

et al. 2018

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Section: Figurementioning

confidence: 99%

Enantioselective Desymmetrization of Cyclobutanones Enabled by Synergistic Palladium/Enamine Catalysis

et al. 2018

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“…This method has yet to be applied to the more challenging cis -isomers 77. A clever approach to enantioenriched trans -2,3-disubstituted cyclobutanones involves desymmetrization of 3-aryl cyclobutanones via an asymmetric deprotonation/alkylation sequence 78. This cyclobutanone functionalization works best with primary alkyl halides, which are good substrates for this S N 2 substitution.…”

Section: Resultsmentioning

confidence: 99%

Applications of 1-Alkenyl-1,1-Heterobimetallics in the Stereoselective Synthesis of Cyclopropylboronate Esters, Trisubstituted Cyclopropanols and 2,3-Disubstituted Cyclobutanones

Hussain

et al. 2009

J. Am. Chem. Soc.

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1-Alkenyl-1,1-heterobimetallics are potentially very useful in stereoselective organic synthesis, but are relatively unexplored. Introduced herein is a practical application of 1-alkenyl-1,1-heterobimetallic intermediates in the synthesis of versatile cyclopropyl alcohol boronate esters, which are valuable building blocks. Thus, hydroboration of 1-alkynyl-1-boronate esters with dicyclohexylborane generates 1-alkenyl-1,1-diboro species. In situ transmetalation with dialkylzinc reagents furnishes 1-alkenyl-1,1-borozinc heterobimetallic intermediates. Addition of the more reactive Zn–C bond to aldehydes generates the key B(pin) substituted allylic alkoxide intermediates. An in situ alkoxide directed cyclopropanation proceeds with the formation of two more C–C bonds, affording cyclopropyl alcohol boronate esters with three new stereocenters in 58–89% isolated yields and excellent diastereoselectivities (>15:1 dr). Oxidation of the B–C bond provides trisubstituted α-hydroxycyclopropyl carbinols as single diastereomers in excellent yields (75–93%). Facile pinacol-type rearrangement of the α-hydroxycyclopropyl carbinols provides access to both cis- and trans-2,3-disubstituted cyclobutanones with high stereoselectivity (>17:1 dr in most cases) from a common starting material. This methodology has been applied in the synthesis of quercus lactones A and B.

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“…First, treatment of ketone 6 j with LiBH 4 resulted in the formation of γ‐butyrolactone 7 . Then, hydrolysis of 7 and subsequent decarboxylation afforded γ‐butyrolactone 8 in 36 % overall yield, which can be converted to (−)‐methyleneolactocin . Although the stereoselectivity of the product was slightly decreased, γ‐butyrolactone 8 was obtained in only three steps from ketone 6 j .…”

Section: Methodsmentioning

confidence: 99%

Diastereoselective Radical Hydroacylation of Alkylidenemalonates with Aliphatic Aldehydes Initiated by Photolysis of Hypervalent Iodine(III) Reagents

Selvakumar

Sakamoto

Maruoka

2016

Chemistry A European J

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Diastereoselective radical hydroacylation of chiral alkylidenemalonates with aliphatic aldehydes is realized by the combination of a hypervalent iodine(III) reagent and UV-light irradiation. The reaction is initiated by the photolysis of hypervalent iodine(III) reagents under mild, metal-free conditions, and is the first example of diastereoselective addition of acyl radicals to olefins to afford chiral ketones in a highly stereoselective fashion. The obtained optically active ketones are useful chiral synthons, as exemplified by the short formal synthesis of (-)-methyleneolactocin.

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An enantioselective synthesis of 3,4-disubstituted butyrolactones

Cited by 50 publications

References 4 publications

Enantioselective Desymmetrization of Cyclobutanones Enabled by Synergistic Palladium/Enamine Catalysis

Enantioselective Desymmetrization of Cyclobutanones Enabled by Synergistic Palladium/Enamine Catalysis

Applications of 1-Alkenyl-1,1-Heterobimetallics in the Stereoselective Synthesis of Cyclopropylboronate Esters, Trisubstituted Cyclopropanols and 2,3-Disubstituted Cyclobutanones

Diastereoselective Radical Hydroacylation of Alkylidenemalonates with Aliphatic Aldehydes Initiated by Photolysis of Hypervalent Iodine(III) Reagents

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