Cycloadditions of chiral carbonyl ylides with imine dipolarophiles as a route to enantiomerically pure α-amino-β-hydroxy acids

Gan, Yu; Harwood, Laurence M.; Richards, Simon C.; Smith, Ian; Vinader, V.

doi:10.1016/j.tetasy.2009.02.029

Cited by 15 publications

(3 citation statements)

References 15 publications

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“…660 Subsequently, reactions with imines were shown to give enantiopure α-amino-β-hydroxy acids. 661 The chiral auxiliary could be recovered and recycled. Padwa and Prien studied the facial selectivity of reactions of dipolarophiles with isomunchnones.…”

Section: Ylide Formation From α-Diazocarbonylsmentioning

confidence: 99%

“…Moderate diastereofacial selectivity and good endo selectivity were observed in reactions with maleimides or dimethyl acetylenedicarboxylate, while excellent diastereofacial and exo selectivity were obtained in reactions with aldehydes, but with slightly lower yields. , The aldehyde-derived adducts could be converted into enantiopure α,β-dihydroxy acids . Subsequently, reactions with imines were shown to give enantiopure α-amino-β-hydroxy acids . The chiral auxiliary could be recovered and recycled.…”

Section: Diazocarbonyl Reactions: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Ford¹,

Miel

Ring³

et al. 2015

Chem. Rev.

1,372

585

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Section: Ylide Formation From α-Diazocarbonylsmentioning

confidence: 99%

Section: Diazocarbonyl Reactions: Introductionmentioning

confidence: 99%

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Ford¹,

Miel

Ring³

et al. 2015

Chem. Rev.

1,372

585

View full text Add to dashboard Cite

“…Among dipolarophiles used in carbonyl ylide cycloadditions, there are few examples of reactions using imines as the dipolarophiles, wherein ethyl diazoacetate, α-aryl-α-diazoesters, and dimethyl diazomalonate have been employed with aldehydes to generate the carbonyl ylides. For example, the first three-component reaction of ethyl diazoacetate, benzaldehyde, and N -benzylidenebenzylamine was demonstrated to afford the oxazolidine cycloadduct via the rhodium(II)-catalyzed carbonyl ylide formation (Scheme a). , High to good yields and high stereoselectivities were achieved with the use of AgSbF 6 in the three-component reaction of ethyl diazoacetate, p -bromobenzaldehyde, and N -benzylideneaniline derivatives, whereas the cycloaddition did not proceed in the absence of the silver salt (Scheme b) .…”

mentioning

confidence: 99%

Three-Component Reactions of Diazoesters, Aldehydes, and Imines Using a Dual Catalytic System Consisting of a Rhodium(II) Complex and a Lewis Acid

et al. 2018

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A dual catalytic system, dirhodium tetrapivalate/ytterbium(III) triflate, enables the three-component reactions of α-alkyl-α-diazoesters, aromatic aldehydes, and N-benzylidenebenzylamine derivatives to afford the corresponding β-amino alcohols in good yields after hydrolysis of the oxazolidine cycloadducts, whereas no β-amino alcohols are obtained in the absence of ytterbium(III) triflate. A similar dual catalytic system, dirhodium tetraacetate/ytterbium(III) triflate, is found to be effective in accelerating the reactions of α-aryl-α-diazoesters in high yields. Furthermore, the reactions using dimethyl diazomalonate are described.

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Cycloadditions of Carbonyl Ylides Derived from Diazocarbonyl Compounds

Hodgson

Muthusamy

2012

Organic Reactions

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[3 + 2] cycloadditions of carbonyl ylides with dipolarophiles provides a synthetically powerful way to make a variety of 5‐membered oxacycles. One of the best ways to generate carbonyl ylide intermediates is by transition metal‐catalyzed loss of nitrogen from diazocarbonyl compounds and trapping of the resultant metallocarbenes by a carbonyl group. This chapter covers the metal‐catalyzed intra‐ and intermolecular cycloadditions of carbonyl ylides derived from diazocarbonyl compounds with various dipolarophiles. The literature up to the end of 2011 is covered. A comprehensive discussion is provided of mechanism and stereochemistry, regioselectivity, stereoselectivity, and asymmetric cycloadditions. The structural scope at the diazo group, of the carbonyl group forming the ylide, and of the dipolarophile is delineated. A systematic analysis is presented of the scope and limitations of intra‐ and intermolecular cycloadditions of cyclic diazocarbonyl‐derived carbonyl ylides from ketones, esters, amides or imides, including cycloadditions of aromatic pyrylium and isomünchnone ylides. The generation of acyclic carbonyl ylides from aldehydes, ketones, or imides and their cycloadditions is also reviewed. Finally, important applications to the total synthesis of natural products and a critical comparison with other methods for carbonyl ylide generation‐cycloaddition are presented.

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Cycloadditions of chiral carbonyl ylides with imine dipolarophiles as a route to enantiomerically pure α-amino-β-hydroxy acids

Cited by 15 publications

References 15 publications

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Three-Component Reactions of Diazoesters, Aldehydes, and Imines Using a Dual Catalytic System Consisting of a Rhodium(II) Complex and a Lewis Acid

Cycloadditions of Carbonyl Ylides Derived from Diazocarbonyl Compounds

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