The Aldol Reaction: Acid and General Base Catalysis

Heathcock, Clayton H.

doi:10.1016/b978-0-08-052349-1.00027-5

Cited by 124 publications

(68 citation statements)

References 218 publications

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“…However, we suspected that the unknown isomer was likely the exo , syn -aldol (i.e., the other exo product formed by stereoelectronically and sterically favored axial attack) [24] or the endo , syn isomer (resulting from the exo – endo inversion of the known exo , anti - 3 , Scheme 2). …”

Section: Resultsmentioning

confidence: 99%

Determination of the relative configuration of tropinone and granatanone aldols by using TBDMS ethers

Łaźny¹,

Nodzewska²,

Sidorowicz³

et al. 2012

Beilstein J. Org. Chem.

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SummaryThe relative configurations of tert-butyldimethylsilyl (TBDMS) ethers of all four diastereomers of the aldols of tropinone (8-methyl-8-azabicyclo[3.2.1]octan-3-one), as well as of granatanone (9-methyl-9-azabicyclo[3.3.1]nonan-3-one), were determined from NMR data, and from the observed interconversion of the diastereomers (exo,anti to endo,syn and exo,syn to endo,anti). The exo forms invert to endo isomers in the presence of silica gel. The relative configuration of a new isomer of tropinone aldol accessible synthetically through the direct solventless reaction of tropinone and benzaldehyde in the presence of water was determined as exo,syn by comparison of NMR data of the aldol isomers, in particular vicinal coupling constants and shifts corresponding to the side-chain CH group, with data of related TBDMS derivatives and confirmed by single-crystal X-ray diffraction.

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Section: Resultsmentioning

confidence: 99%

Determination of the relative configuration of tropinone and granatanone aldols by using TBDMS ethers

Łaźny¹,

Nodzewska²,

Sidorowicz³

et al. 2012

Beilstein J. Org. Chem.

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“…The residual crude product was purified by column chromatography on silica gel to afford a mixture of the aldol adducts; yield: 130.1 mg (99%). The diastereomeric ratio was determined to be 66:34 by 1 H NMR analysis. The enantioselectivity of the major isomer was determined to be 74% ee by HPLC analysis using a chiral column (Daicel Chiralcel OD-H, hexane/i-PrOH = 99/1, flow rate = 1.0 mL min À19.78 (c 1.0, CHCl 3 , major isomer).…”

Section: Experimental Section General Remarksmentioning

confidence: 99%

“…[1] In order to obtain aldol products in high yield and satisfactory optical purity, various methods using chiral catalysts have been developed. [2][3][4] In particular, the application of ketones as electrophiles to the asymmetric transformation has recently attracted the attention of synthetic organic chemists, because products possessing a chiral tertiary alcohol moiety are synthetically useful.…”

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confidence: 99%

Asymmetric Aldol Reaction of Ketones with Alkenyl Trichloroacetates Catalyzed by Dibutyltin Dimethoxide and BINAP⋅Silver(I) Complex: Construction of a Chiral Tertiary Carbon Center

et al. 2009

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A novel aldol reaction of alkenyl trichloroA C H T U N G T R E N N U N G acetates with a-keto esters was realized by using dibutyltin dimethoxide as a catalyst, which was regenerated by the addition of methanol. The reaction was found to be remarkably accelerated by the addition of a catalytic amount of a bidentate phosphine·silver(I) complex. Use of the BINAP·sil-ver triflate (AgOTf) complex as the chiral co-catalyst resulted in the formation of optically active aldol products possessing a chiral tertiary carbon with up to 93% ee. This catalytic method was further applied to the asymmetric reaction of diketene with methyl benzoylformate.

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“…1 In light of current worldwide interests to adopt green and cost-effective chemical processes, researchers have been intensively attempting to develop C-C bond-forming reactions that are generic, selective, reliable, and scalable, and involve chemical transformations with atom-economy and minimal waste production. One successful approach to achieve this goal includes the development of catalysts that are capable of efficiently transforming C-C bond-forming reactions such as the Diels-Alder, 2 Grignard, 3 Wittig, 4, 5 Heck, 6 Sonogashira, 7 Suzuki, and Suzuki-Miyaura, 8,9 Stille, 10, 11 aldol, 12, 13 Knoevenagel,14 and Henry reactions. 15 Currently, these catalytic reactions are reported to undergo in the presence of either homogeneous or heterogeneous-type catalysts.…”

Section: Introductionmentioning

confidence: 99%