Structures of Marvel's .delta.-lactone and polymer

Rowland, Alex T.; Gill, Benjamin C.

doi:10.1021/jo00237a042

Cited by 17 publications

(27 citation statements)

References 2 publications

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“…When quinine was used, the trans isomer 2 [12] was formed in 44 % yield, with a good diastereoselective ratio and 65 % ee (Entry 1). The reaction carried out by using stoichiometric amounts of quinine under more diluted conditions afforded compound 2a in 43 % yield and 72 % ee (Entry 2).…”

Section: Resultsmentioning

confidence: 99%

Quinine‐Catalysed Double Michael Addition of Malononitrile to 1,5‐Disubstituted Pentadien‐3‐ones: A Stereoselective Route to Cyclohexanones

Fusco

Lattanzi

2011

Eur J Org Chem

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The stereoselective synthesis of 4‐oxo‐2,6‐diaryl‐cyclohexane‐1,1‐dicarbonitriles has been developed through double Michael addition of malononitrile to 1,5‐disubstituted pentadien‐3‐ones catalysed by quinine. This simple cascade process affords cyclohexanones in moderate‐to‐good yields, excellent diastereoselectivity and up to 86 % ee. The isolation of the monoaddition product helps to shed light on thestereochemical outcome of the two‐step process.

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Section: Resultsmentioning

confidence: 99%

Quinine‐Catalysed Double Michael Addition of Malononitrile to 1,5‐Disubstituted Pentadien‐3‐ones: A Stereoselective Route to Cyclohexanones

Fusco

Lattanzi

2011

Eur J Org Chem

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“…[5+1] annulation is a novel strategy for the construction of six-membered cyclic compounds and total synthesis of natural products (Rowland & Gill, 1988;Wu et al, 2011;Li et al, 2011). The regiospecific [5+1] annulation reactions have drawn much attentions and both the five-carbon 1,5-bielectrophiles and the one-atom nucleophiles been explored extensively (Bi et al, 2005;Zhao et al, 2006;Fu et al, 2009;Xu et al, 2012).…”

Section: S2 Results and Discussionmentioning

confidence: 99%

“…For the synthesis, see: Zhang et al (2010); Tan et al (2009). For related structures, see: Rowland & Gill (1988); Aleman et al (2009); Wu et al (2011); Li et al (2011). For other [5 + 1] annulation reactions, see: Bi et al (2005); Zhao et al (2006); Fu et al (2009); Xu et al (2012).…”

Section: Related Literaturementioning

confidence: 99%

Ethyl 2,6-bis(4-chlorophenyl)-1-isocyano-4-oxocyclohexanecarboxylate

et al. 2014

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In the title compound, C22H19Cl2NO3, the central six-membered ring is in a twist-boat conformation. The two aryl groups are in equatorial positions, trans to each other and with a dihedral angle of 77.50 (2)° between them. One of the least hindered –CH2– groups and one of the aryl-substituted C atoms, with its axial H atom, are in the flagpole positions. The ethoxycarbonyl group is in an equatorial position and is cis to the second aryl group. In the crystal, molecules are linked via weak C—H⋯O hydrogen bonds, forming chains along [010].

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“…For the synthesis, see: Tan et al (2009); Zhang et al (2010). For related structures, see: Rowland & Gill (1988); Rowland et al (1998); Aleman et al (2009). Cyclic constrained analogues of phenylalanine (Phe) are of particular interest in the construction of peptide analogues with controlled folds in the backbone because they play an important role in both restricting the 1 torsion angle and in peptide receptor recognition processes, see: Cativiela & Díaz-de-Villegas (1998, 2000, 2007; Cativiela & Ordó ñ ez (2009); Lasa & Cativiela (2006).…”

Section: Related Literaturementioning

confidence: 99%