<i>meso</i>-4,5-Dihydroxy-4,5-dimethylocta-1,7-diyne

Bolte, Michael; Eckstein, Klaus; Hashmi, A. Stephen K.

doi:10.1107/s1600536805036147

Cited by 1 publication

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References 6 publications

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“…The structural assignment of the syn isomers is based on the comparison of the NMR data and the configuration observed in several Xray crystal structure analyses. [7,8] As one representative example, Figure 1 displays the solid-state structure of syn-2 b (other solid-state structures of syn-diols 2 c and 2 f have been obtained, too). [7] The propargyl side chain shows two different orientations in the solid state.…”

Section: Resultsmentioning

confidence: 99%

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Gold Catalysis: Tandem Reactions of Diyne–Diols and External Nucleophiles as an Easy Access to Tricyclic Cage‐Like Structures

Hashmi

Bührle

Wölfle

et al. 2010

Chemistry A European J

131

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Different diyne-diols composed of two terminal homopropargylic alcohol groups were prepared by bi-directional synthesis. Subjection of the syn diastereomers to NAC-gold catalysts (NAC=nitrogen acyclic carbene) in the presence of external nucleophiles such as water or anilines provided substituted and highly rigid heterocyclic cages. The corresponding anti disastereomers polymerised. An intermediate of the reactions of the syn diastereomers could be isolated and even be characterised by crystal structure analysis. Overall, eight new bonds are formed in the reaction, which proceeds by a multistep sequence of highly selective hydroalkoxylations and hydrohydroxylation or hydroaminations. For furyl substituents and for internal alkynes competing reaction pathways could be identified. By the cross-coupling of a product with an iodoaryl substituent, the use of these cage compounds as geometrically defined linking groups by using orthogonal transition-metal-catalysed methodology, namely, gold and palladium catalysis, could be demonstrated.

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Section: Resultsmentioning

confidence: 99%

“…(Table 4, entry 6). A massive counterion effect was visible by changing the counterion to hexafluoroantimonate; in these cases no reaction took place under various conditions (Table 4, entries [7][8][9][10].…”

Section: Full Papermentioning

confidence: 99%

Gold Catalysis: Tandem Reactions of Diyne–Diols and External Nucleophiles as an Easy Access to Tricyclic Cage‐Like Structures

Hashmi

Bührle

Wölfle

et al. 2010

Chemistry A European J

131

View full text Add to dashboard Cite

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meso-4,5-Dihydroxy-4,5-dimethylocta-1,7-diyne

Abstract: Molecules of the title compound, C10H14O2, are connected by intermolecular hydrogen bonds, forming zigzag chains running in the b‐axis direction. In addition, the two hydroxyl groups form an intramolecular hydrogen bond.

Cited by 1 publication

References 6 publications

Gold Catalysis: Tandem Reactions of Diyne–Diols and External Nucleophiles as an Easy Access to Tricyclic Cage‐Like Structures

Gold Catalysis: Tandem Reactions of Diyne–Diols and External Nucleophiles as an Easy Access to Tricyclic Cage‐Like Structures

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meso-4,5-Dihydroxy-4,5-dimethylocta-1,7-diyne

Abstract: Mol­ecules of the title compound, C10H14O2, are connected by inter­molecular hydrogen bonds, forming zigzag chains running in the b‐axis direction. In addition, the two hydroxyl groups form an intra­molecular hydrogen bond.

Cited by 1 publication

References 6 publications

Gold Catalysis: Tandem Reactions of Diyne–Diols and External Nucleophiles as an Easy Access to Tricyclic Cage‐Like Structures

Gold Catalysis: Tandem Reactions of Diyne–Diols and External Nucleophiles as an Easy Access to Tricyclic Cage‐Like Structures

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Product

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Abstract: Molecules of the title compound, C10H14O2, are connected by intermolecular hydrogen bonds, forming zigzag chains running in the b‐axis direction. In addition, the two hydroxyl groups form an intramolecular hydrogen bond.