Enantioselective Synthesis of 4‐Hydroxy‐2‐cyclohexenones through a Multicomponent Cyclization

Barluenga, José; Suero, Marcos G.; Campa, Raquel de la; Flórez, Josefa

doi:10.1002/anie.201004413

Cited by 20 publications

(3 citation statements)

References 45 publications

(6 reference statements)

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“…128 More specific transformations include the asymmetric propargylboration of aldehydes using 10-trimethylsilyl-9borabicyclo[3.3.2]decanes, 129 or Barluenga's multicomponent reaction of chromium carbenes 73, oxazolidine-2-ones lithium enolates 74, and Grignard reagents 75 to yield highly substituted cyclohexenones 76 bearing allenolic units. 130 Central-to-central chirality transfer is reported, using optically pure oxazolidines as chiral inductors, and yielding allenols 76 showing up to 99% ee (Scheme 16).…”

Section: Enantioenriched Allenolsmentioning

confidence: 99%

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

2021

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The allene functionality has participated in one of the most exciting voyages in organic chemistry, from chemical curiosities to a recurring building block in modern organic chemistry. In the last decades, a special kind of allene, namely, allenol, has emerged. Allenols, formed by an allene moiety and a hydroxyl functional group with diverse connectivity, have become common building blocks for the synthesis of a wide range of structures and frequent motif in naturally occurring systems. The synergistic effect of the allene and hydroxyl functional groups enables allenols to be considered as a unique and sole functionality exhibiting a special reactivity. This Review summarizes the most significant contributions to the chemistry of allenols that appeared during the past decade, with emphasis on their synthesis, reactivity, and occurrence in natural products.

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Section: Enantioenriched Allenolsmentioning

confidence: 99%

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

2021

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“…In 2010, Barluenga et al reported an enantioselective synthesis of 4-hydroxy-2-cyclohexenones 510 through a four-component reaction, occurring between aryl- and heteroarylcarbene chromium complexes 511 , in situ-prepared lithium enolate of ( S )-3-acetyl-4-benzyl-2-oxazolidinone 512 , and 2 equiv of propargylic organomagnesium bromides 513 . This remarkable domino process afforded the corresponding almost enantiopure densely functionalized 2-cyclohexenones 510 containing two quaternary stereogenic centers at the α- and γ-positions.…”

Section: Multicomponent Reactionsmentioning

confidence: 99%

Stereocontrolled Domino Reactions

2012

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AS 2.8.4. Other Domino Reactions AT 3. Multicomponent Reactions AU 3.1. Multicomponent Reactions Initiated by the Michael Reaction AU 3.1.1. Multicomponent Reactions Initiated by a Classical Michael Reaction AU 3.1.2. Multicomponent Reactions Initiated by a Hetero-Michael Reaction AW 3.2. Multicomponent Hantzsch Reactions AZ 3.3. Multicomponent Ugi Reactions AZ 3.4. Multicomponent Strecker Reactions BG 3.5. Multicomponent Mannich Reactions BH 3.6. Multicomponent Reactions Initiated by an Allylation Reaction BI 3.7. Multicomponent Passerini Reactions BK 3.8. Multicomponent Biginelli Reactions BM 3.9. Multicomponent Petasis Reactions BN 3.10. Miscellaneous Multicomponent Reactions BP 3.10.1. Metal-Catalyzed Multicomponent Reactions BP 3.10.2. Other Multicomponent Reactions BT 4. Conclusion BZ Author Information BZ Biography CA Abbreviations CA References CA

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“…224 In 2010, Barluenga et al reported an enantioselective synthesis of 4-hydroxy-2-cyclohexenones through a four-component reaction, occurring among aryl-and heteroarylcarbene chromium complexes, in situ prepared lithium enolate of (S)-3-acetyl-4-benzyl-2-oxazolidinone, and two equivalents of propargylic organomagnesium bromides. 225 process afforded the corresponding almost enantiopure densely functionalised 2-cyclohexenones containing two quaternary stereogenic centres at the a and g positions. As shown in Scheme 1.136, these products were produced in moderate to high yields as single stereoisomers in all cases of substrates studied.…”

Section: Multicomponent Reactions Based On the Petasis Reactionmentioning

confidence: 99%

Asymmetric Domino Reactions Based on the Use of Chiral Substrates

2013

Asymmetric Domino Reactions

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This chapter updates the recent developments in asymmetric one-, two-, and multicomponent domino reactions which involve chiral substrates. It is divided into two sections, dealing successively with one- and two-component domino reactions, and with multicomponent domino reactions. The first section is subdivided into eight sections, describing domino reactions with an anionic primary step, domino reactions based on cationic sequences, domino reactions initiated by a pericyclic primary step, domino reactions based on carbene sequences, palladium-catalysed domino reactions, ruthenium-catalysed domino reactions, gold-catalysed domino reactions, and finally miscellaneous domino reactions. The second section of the chapter is subdivided into 10 sections, dealing with multicomponent reactions initiated by the Michael addition, multicomponent reactions based on the Hantzsch reaction, multicomponent reactions based on the Ugi reaction, multicomponent reactions based on the Strecker reaction, multicomponent reactions based on the Mannich reaction, multicomponent reactions initiated by an allylation reaction, multicomponent reactions based on the Passerini reaction, multicomponent reactions based on the Biginelli reaction, multicomponent reactions based on the Petasis reaction, and finally miscellaneous multicomponent reactions. The power and utility of these reactions are well illustrated by their application in the synthesis of a wide range of structurally diverse and complex chiral molecules.

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Enantioselective Synthesis of 4‐Hydroxy‐2‐cyclohexenones through a Multicomponent Cyclization

Cited by 20 publications

References 45 publications

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

Stereocontrolled Domino Reactions

Asymmetric Domino Reactions Based on the Use of Chiral Substrates

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