A New Method for Expeditious Ketone Synthesis from Acids via Acyl Hemiacetals

Mattson, Matthew N.; Rapoport, Henry

doi:10.1021/jo9607471

Cited by 37 publications

(18 citation statements)

References 34 publications

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“…Otherwise, the reaction between the unsaturation fixed on the acid chain could take place more favorably with the vinyl group to form a 6-allylpyrone structure compared to the reaction involving the allyl rest leading to a 7-vinyl caprolactone. [14,16,17] Treatment of 13 with alcohol 14a in the presence of Grubbs type II catalyst 5 afforded dimer structure 18, ketone 19 [18] resulting from the isomerization of the terminal double bond [19] and further reketonization, and also 5064 Scheme 3. Retrosynthetic analyses for 3 and related 6-allyl hexenolides 12.…”

Section: Resultsmentioning

confidence: 99%

Regioselective Tandem Ring Closing/Cross Metathesis of 1,5‐Hexadien‐3‐ol Derivatives: Application to the Total Synthesis of Rugulactone

2010

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Section: Resultsmentioning

confidence: 99%

Regioselective Tandem Ring Closing/Cross Metathesis of 1,5‐Hexadien‐3‐ol Derivatives: Application to the Total Synthesis of Rugulactone

2010

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“…However, undesired removal of Thp from other amino acids was observed during aqueous work‐up. This could be attributed to the high lability of the hemiacetal esters, as previously described . Therefore, after monitoring the reaction to completion by using thin‐layer chromatography, N , N ‐diisopropylethylamine (DIEA) was added as a part of the work‐up to neutralize the PTSA used during the reaction.…”

Section: Thp Protection Of the Carboxyl Groupmentioning

confidence: 99%

“…This could be attributed to the high lability of the hemiacetal esters, as previously described. [60,74,75] Therefore, after monitoring the reaction to completion by using thin-layer chromatography, N,N-diisopropylethylamine (DIEA) was added as ap art of the work-up to neutralize the PTSA used during the reaction. The crude product was then purified directly on basic silica using n-hexane and ethyl acetate (1:1) as as olvent system-an approach that afforded the pure compounds, whichw ere then characterized by NMR spectroscopy.…”

Section: Introduction Of the Protecting Groupmentioning

confidence: 99%

Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry

et al. 2017

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Tetrahydropyranyl (Thp) is recognized as a useful protecting group for alcohols in organic synthesis. It has several advantages, including low cost, ease of introduction, general stability to most non‐acidic reagents, it confers good solubility, and the ease with which it can be removed if the functional group it protects requires manipulation. However, little attention has been paid to Thp in peptide chemistry. Provided here is a concise analysis of the Thp protection of various amino acid functionalities (OH, SH, NH and COOH) and its application to peptide synthesis. Thp is a useful moiety for the side‐chain protection of serine, threonine and cysteine and is suitable for the Fmoc/tBu solid‐phase peptide synthesis strategy. The immobilized version of 3,4‐dihydro‐2H‐pyran, the so‐called Ellman resin, is also discussed as a useful solid support for anchoring the side chains of serine, threonine and tryptophan residues.

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“…IR (KBr): 3060, 3029, 2905, 1686, 1449, 1338, 1219, 1202, 753, 730, 700, 688 cm -1 . MS (EI) m/z (relative intensity) 196 (8) [M + ], 165 (6), 105 (100), 91 (19), 77 (48), 65 (12), 51 (14).…”

Section: S3mentioning

confidence: 99%

TiCl₄‐Catalyzed Indirect anti‐Markovnikov Hydration of Alkynes: Application to the Synthesis of Benzo[b]furans.

Ackermann

Kaspar

2007

ChemInform

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Hydration O 0335TiCl4-Catalyzed Indirect anti-Markovnikov Hydration of Alkynes: Application to the Synthesis of Benzo[b]furans. -TiCl 4 -mediated treatment of internal alkynes of type (I), (V), (IX), and (XIII) with aromatic amines followed by hydrolysis allows a simple, efficient, and selective formation of anti-Markovnikov hydration products. The ketones containing an ortho-halogenated benzylic unit can smoothly be converted into benzofuran derivatives. In contrast, sterically hindered 1-phenyl-3,3-dimethylbutyne predominantly yields the Markovnikov product instead of the anti-Markovnikov derivative. -(ACKERMANN*, L.; KASPAR, L. T.; J.

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A New Method for Expeditious Ketone Synthesis from Acids via Acyl Hemiacetals

Cited by 37 publications

References 34 publications

Regioselective Tandem Ring Closing/Cross Metathesis of 1,5‐Hexadien‐3‐ol Derivatives: Application to the Total Synthesis of Rugulactone

Regioselective Tandem Ring Closing/Cross Metathesis of 1,5‐Hexadien‐3‐ol Derivatives: Application to the Total Synthesis of Rugulactone

Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry

TiCl₄‐Catalyzed Indirect anti‐Markovnikov Hydration of Alkynes: Application to the Synthesis of Benzo[b]furans.

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A New Method for Expeditious Ketone Synthesis from Acids via Acyl Hemiacetals

Cited by 37 publications

References 34 publications

Regioselective Tandem Ring Closing/Cross Metathesis of 1,5‐Hexadien‐3‐ol Derivatives: Application to the Total Synthesis of Rugulactone

Regioselective Tandem Ring Closing/Cross Metathesis of 1,5‐Hexadien‐3‐ol Derivatives: Application to the Total Synthesis of Rugulactone

Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry

TiCl4‐Catalyzed Indirect anti‐Markovnikov Hydration of Alkynes: Application to the Synthesis of Benzo[b]furans.

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Product

Resources

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TiCl₄‐Catalyzed Indirect anti‐Markovnikov Hydration of Alkynes: Application to the Synthesis of Benzo[b]furans.