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1 article(s) from Schlirf, Jens

Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes

M. Emin Cinar,
Bernward Engelen,
Martin Panthöfer,
Hans-Jörg Deiseroth,
Jens Schlirf and
Michael Schmittel

Beilstein J. Org. Chem. 2016, 12, 813–824, doi:10.3762/bjoc.12.80

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Scheme 1: Synthesis of racemic tetrahydro-2H-pyran-2,4-diols rac-5 from enolates 2 and aldehydes 3.

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Scheme 2: Synthesis of rac-5a–j and monoaldol products 6a–i and 6ac–ic as obtained from propiophenone (1a) in...

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Figure 1: Crystal structure of enantiopure 5a [40].

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Scheme 3: Reaction of various ketones (1b−i) with benzaldehyde (3a) in the presence of InCl₃ and ZrCl₄.

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Figure 2: (a) Crystal structure of 7h and (b) its arrangement in the crystal [43].

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Scheme 4: Reaction of n-butyrophenone (1f) with various aldehydes (3b−d) in presence of InCl₃ (reaction time:...

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Scheme 5: Domino aldol reactions of different aldehydes and ketones possessing p-H, p-F and p-MeO substituent...

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Scheme 6: DFT calculations on the formation of A3, hydrolysis of which provides 5a, at M06/6-31G(d)/LANL2DZ//...

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Scheme 7: The follow-up reactions of A2_OH and 6a at M06/6-31G(d)//B3LYP/6-31G(d) level (ΔG_rel with unscaled z...

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Scheme 8: Proposed mechanism for the formation of benzaldehyde in the reaction of 9-anthracenylaldehyde (3f) ...

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Published 27 Apr 2016

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