Diastereotopic group selective intramolecular conjugate addition of 4-(2-hydroxyethyl)-p-quinol derivatives: Synthesis of the optically pure cis-7-oxabicyclo[4.3.0]non-2-en-4-one skeleton

Fujioka, Hiromichi; Kitagaki, Shinji; Ohno, Naoko; Kitagawa, Hajime; Kita, Yasuyuki; Matsumoto, Keita

doi:10.1016/s0957-4166(00)86199-6

Cited by 15 publications

(11 citation statements)

References 18 publications

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“…Even more remarkable are the stereospecificity and the effective diastereotopic CC bond selection observed. A similar diastereoselective process on p -quinols directed by the OH was found in Grignard additions to their lithium alkoxides in racemic series, but the dienone desymmetrization of an optically active p -quinol had only been achieved in an intramolecular conjugate addition …”

mentioning

confidence: 69%

Diastereoselective Uncatalyzed Conjugate Addition of Organoaluminum Reagents: Efficient Desymmetrization of (R)-[(p-Tolylsulfinyl)methyl]quinols

Ribagorda

et al. 1996

J. Org. Chem.

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confidence: 69%

Diastereoselective Uncatalyzed Conjugate Addition of Organoaluminum Reagents: Efficient Desymmetrization of (R)-[(p-Tolylsulfinyl)methyl]quinols

Ribagorda

et al. 1996

J. Org. Chem.

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“…Synthesis of 4-[( p -Tolylsulfinyl)methyl]- p -quinols. The preparation of p -quinols is based on the oxidation of phenols and phenol ethers and can be achieved by either electrochemical, chemical, or photooxidation methods. The addition of organometallic derivatives to quinones or quinone monoketals has also been successfully used in the synthesis of these compounds.…”

mentioning

confidence: 99%

π-Facial Diastereoselection in Diels−Alder Reactions of (R)-4-[(p-Tolylsulfinyl)methyl]quinols

1997

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Diels−Alder reactions of a range of (R)-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienones with cyclopentadiene and 1,3-pentadiene proceed in a total π-facial diastereoselective manner from the C-4 OH side. Ab initio calculations at the RHF/6-31G* theory level provide data on transition-state energies for cycloadditions with cyclopentadiene in full agreement with the experimental results.

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“…Deprotection of dienone 10 provided bicyclic furan 11 in quantitative yield as a mixture of diastereoisomers (11a/11b, 4.5:1). 7 Better selectivities were recently reported by Node for a group-selective 1,4-phenol addition onto a dienone (12 → 13). 8…”

Section: Michael Additionsmentioning

confidence: 85%

Desymmetrization and Diastereotopic Group Selection in 1,4-Cyclohexadienes

Studer¹,

Schleth²

2005

Synlett

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Diastereotopic group selection in 1,4-cyclohexadienes is a useful approach to synthesize rather complex compounds in a single operation. The stereoinduction occurs via a covalently bound stereogenic center. Cycloadditions, Michael additions, and radical reactions have been conducted as group-selective processes. Even more elegant is the desymmetrization of an achiral 1,4-cyclohexadiene. Various chiral reagents have been used successfully to desymmetrize 1,4-cyclohexadienes. In one step, at least two new stereogenic centers are formed. Chiral quaternary carbon centers can be obtained with high selectivity. This Account will provide an overview on diastereotopic group selection and desymmetrization in various 1,4-cyclohexadiene derivatives.

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Diastereotopic group selective intramolecular conjugate addition of 4-(2-hydroxyethyl)-p-quinol derivatives: Synthesis of the optically pure cis-7-oxabicyclo[4.3.0]non-2-en-4-one skeleton

Cited by 15 publications

References 18 publications

Diastereoselective Uncatalyzed Conjugate Addition of Organoaluminum Reagents: Efficient Desymmetrization of (R)-[(p-Tolylsulfinyl)methyl]quinols

Diastereoselective Uncatalyzed Conjugate Addition of Organoaluminum Reagents: Efficient Desymmetrization of (R)-[(p-Tolylsulfinyl)methyl]quinols

π-Facial Diastereoselection in Diels−Alder Reactions of (R)-4-[(p-Tolylsulfinyl)methyl]quinols

Desymmetrization and Diastereotopic Group Selection in 1,4-Cyclohexadienes

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