High Diastereoselectivity Induced by a Fluorous Alkyl Group in the Asymmetric Michael Reaction of Nitroalkenes Catalyzed by a Prolinol Methyl Ether

Funabiki, Kazumasa; Ohta, Masaya; Sakaida, Yuta; Oida, K.; Kubota, Yasuhiro; Matsui, Masaki

doi:10.1002/ajoc.201300171

Cited by 6 publications

(2 citation statements)

References 60 publications

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“…They also prepared prolinol methyl ether 38, which is the derivative of prolinol 36, and investigated its application as an asymmetric organocatalyst for the Michael reactions of nitroalkenes with aldehydes (Scheme 32). 47 The diastereoselectivity with 38 was much higher than that with non-uorinated prolinol methyl ethers 39 and 40, which have two n-octyl groups or two phenyl groups respectively in place of (peruorohexyl)ethyl groups. From the advantageous point of reusability, the catalyst 38 was recoverable by solid-phase extraction using uorous reverse-phase silica gel.…”

Section: Application Of Perfluoroalkylated Molecular Catalysts To Asy...mentioning

confidence: 94%

Enhancement of stereoselectivities in asymmetric synthesis using fluorinated solvents, auxiliaries, and catalysts

et al. 2015

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Section: Application Of Perfluoroalkylated Molecular Catalysts To Asy...mentioning

confidence: 94%

Enhancement of stereoselectivities in asymmetric synthesis using fluorinated solvents, auxiliaries, and catalysts

et al. 2015

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“…This supported catalyst has also been implemented in continuous flow processes. Furthermore, an ionically-tagged diphenylprolinol silyl ether has been employed in three different Michael additions of aldehydes to nitroolefins in ionic liquids, although its recyclability was very limited [ 47 ], similar to when a prolinol methyl ether carrying two perfluorohexylethyl groups was used as catalyst to give 2 (R 1 = alkyl, R 2 = alkyl, aryl), being recovered in only 40% by fluorous reverse-phase silica gel [ 48 ].…”

Section: Carbon Nucleophilesmentioning

confidence: 99%

Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes

et al. 2017

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The asymmetric conjugate addition of carbon and heteroatom nucleophiles to nitroalkenes is a very interesting tool for the construction of highly functionalized synthetic building blocks. Thanks to the rapid development of asymmetric organocatalysis, significant progress has been made during the last years in achieving efficiently this process, concerning chiral organocatalysts, substrates and reaction conditions. This review surveys the advances in asymmetric organocatalytic conjugate addition reactions to α,β-unsaturated nitroalkenes developed between 2013 and early 2017.

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The Catalytic, Enantioselective Michael Reaction

et al. 2016

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The catalytic enantioselective Michael reaction is the conjugate addition of a resonance‐stabilized carbanion to an electron‐poor olefin (an αβ‐unsaturated carbonyl compound or a related derivative) mediated by substoichiometric amounts of a chiral catalyst that enables stereocontrol in the newly generated stereocenter(s). This reaction allows the direct enantioselective construction of substituted 1,5‐dicarbonyl compounds or related architectures through the appropriate selection of the enolizable carbonyl compound employed as pronucleophile and the Michael acceptor. A variety of catalyst architectures have been described that make it possible to carry out this reaction with superior levels of chemical efficiency and high enantio‐ and stereocontrol, and also under conditions that tolerate a wide variety of functional groups. Both transition metal catalysis and organocatalysis have been employed as methodological approaches for carrying out this reaction in an enantioselective manner. This chapter describes different catalytic systems and methods developed for achieving enantioselective Michael reactions through the end of 2012, including a detailed mechanistic explanation of the different generic modes of substrate activation operating with each type of catalyst and their associated stereochemical aspects. The intention is to provide researchers interested in applying this methodology to their own synthetic strategies with a suitable starting point for identifying an efficient synthetic approach. In addition, the preparation of selected catalysts that are excellent for a particular pairing of substrates in this reaction, together with practical experimental protocols are described and some examples in which these methodologies have been applied to total synthesis have been included. This chapter is limited exclusively to those examples in which the final Michael addition product is obtained after protonation of the conjugate addition intermediate and therefore, tandem, domino, or cascade processes initiated by Michael reactions lie outside the scope of this work. Supplemental references are provided for articles published after the 2012 cut‐off date through the first half of 2015.

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High Diastereoselectivity Induced by a Fluorous Alkyl Group in the Asymmetric Michael Reaction of Nitroalkenes Catalyzed by a Prolinol Methyl Ether

Cited by 6 publications

References 60 publications

Enhancement of stereoselectivities in asymmetric synthesis using fluorinated solvents, auxiliaries, and catalysts

Enhancement of stereoselectivities in asymmetric synthesis using fluorinated solvents, auxiliaries, and catalysts

Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes

The Catalytic, Enantioselective Michael Reaction

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