Asymmetric synthesis employing chiral ketones as templates

Uang, Biing‐Jiun; Po, Shy-Yau; Hung, Shang‐Cheng; Liu, Hung-Hsin; Hsu, Chin-Yun; Lin, Yi-Sho; Chang, Jia‐Wen

doi:10.1351/pac199769030615

Cited by 13 publications

(4 citation statements)

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“…The hydroboration of chiral allenes 671 yielded allylic alcohols 673 or 674 upon oxidation of the in-situ formed allylic borane 672 (Scheme ) 139 …”

Section: Hydrometalation Reactionsmentioning

confidence: 99%

Some Typical Advances in the Synthetic Applications of Allenes

2005

Chem. Rev.

1,310

256

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In 1989, Kakiuchi et al. reported that under irridation propadiene can undergo [2+2]-cycloaddition with R,β-unsaturated cyclohexenones to afford methylene-cyclobutane-containing bicyclic products 1 (Scheme 1). 6 Shi et al. reported that under the catalysis of DABCO, N-tosylated imines 2 can undergo [2+2]cycloaddition with 2,3-butadienoate or 3,4-pentadien-2-one to afford azetidine derivatives 3. 7 The reaction proceeded via the nucleophilic addition of DABCO to the electron-deficient allene forming 4-and 5-type intermediate, which may undergo 1,2-addition with the imines to afford 6. Intramolecular conjugate Scheme 1

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“…The hydroboration of chiral allenes 671 yielded allylic alcohols 673 or 674 upon oxidation of the in-situ formed allylic borane 672 (Scheme ) 139 …”

Section: Hydrometalation Reactionsmentioning

confidence: 99%

Some Typical Advances in the Synthetic Applications of Allenes

2005

Chem. Rev.

1,310

256

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“…Among the methodologies developed in the asymmetric aldol reaction, , the version that uses carboxylic acid derived chiral enolates still continues to have extensive synthetic applications . Well-established examples of the latter are the Evans α-amino acid derived N -acyloxazolidinones 5 and the Oppolzer's N -acylcamphorsultam derivatives .…”

Section: Introductionmentioning

confidence: 99%

Highly Diastereoselective Aldol Reactions with Camphor-Based Acetate Enolate Equivalents

et al. 1999

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New lithium enolates of alpha-hydroxy ketones, derived from camphor, are evaluated for asymmetric aldol reactions in the presence of lithium chloride. The diastereoselectivity of the reactions between the lithium enolate of 3 and a variety of achiral aldehydes is strongly influenced by the lithium chloride salt. In these instances, the achieved levels of asymmetric induction, typically 95:5 dr, are in the range of those attained in aldol reactions involving the lithium enolate of the methyl ketone 4, which is sterically more demanding. The resulting aldol adducts are easily transformed into beta-hydroxy carboxylic acids, ketones, and aldehydes with concomitant recovery of the camphor, the chiral controller of the process, which can be reused.

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“…Wieland–Miescher ketones and their C(5) homologs are important chiral building blocks in natural products synthesis (Ling et al .,; Enders, ). Chiral aldehydes and ketones are important building blocks (or intermediates) and play important roles in asymmetric synthesis (Uang, et al ., ). Both indirect (Dehmlow and Sauerbier, ; Toyo'oka and Liu ); direct (Hyun et al ., ; Johnson and Wainer, ; Zhou et al ., ) approaches have been employed for enantioseparation of carbonyl compounds.…”

Section: Introductionmentioning

confidence: 99%

(S)‐Naproxen as a platform to develop chiral derivatizing reagent for reversed‐phase high‐performance liquid chromatographic enantioseparation of analytes having a carbonyl functional group

Bhushan

Lal

2012

Biomedical Chromatography

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(S)-Naproxen was used to synthesize a chiral reagent, (S)-2-(6-methoxynaphthalen-2-yl)propanehydrazide, by itsreaction with hydrazine hydrate in the presence of dicyclohexylcarbodiimide as coupling agent. The reagent was characterized and its chiral purity was established. It was used as a chiral derivatizing reagent for the synthesis of hydrazone diastereomers, under microwave irradiation, of certain chiral aldehydes and ketones. The respective diastereomers were separated by reversed-phase high-performance liquid chromatography using a binary solvent combination containing trifluoroacetic acid. The diastereomers were detected at 231 nm. The method was validated for accuracy, precision, and limit of detection (LOD). For a series of hydrazones the LOD was found to be in the range 1.62-1.65 pmol/mL.

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Asymmetric synthesis employing chiral ketones as templates

Abstract: Abstract

Cited by 13 publications

References 1 publication

Some Typical Advances in the Synthetic Applications of Allenes

Some Typical Advances in the Synthetic Applications of Allenes

Highly Diastereoselective Aldol Reactions with Camphor-Based Acetate Enolate Equivalents

(S)‐Naproxen as a platform to develop chiral derivatizing reagent for reversed‐phase high‐performance liquid chromatographic enantioseparation of analytes having a carbonyl functional group

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