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Search for "acyloin rearrangement" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

α-Ketol and α-iminol rearrangements in synthetic organic and biosynthetic reactions

Scott Benz and
Andrew S. Murkin

Beilstein J. Org. Chem. 2021, 17, 2570–2584, doi:10.3762/bjoc.17.172

, tandem reactions, and the total synthesis and biosynthesis of natural products. This review explores the use of α-ketol rearrangements in these contexts over the past two decades. Keywords: acyloin rearrangement; asymmetric synthesis; iminol rearrangement; ketol rearrangement; tandem reactions

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Graphical Abstract

Figure 1: Generalized α-ketol or α-iminol rearrangement.

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Figure 2: Nickel(II)-catalyzed enantioselective rearrangement of ketol 3 to form the ring-expanded and chiral...

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Figure 3: Enantioselective ring expansion of β-hydroxy-α-dicarbonyl 6 catalyzed by a chiral copper-bisoxazoli...

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Figure 4: Enantioselective rearrangement of ketols 9 and 12 and hydroxyaldimine 14 catalyzed by Al(III) or Sc...

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Figure 5: Asymmetric rearrangement of α,α-dialkyl-α-siloxyaldehydes 16 to α-siloxyketones 17 catalyzed by chi...

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Figure 6: BF₃-promoted diastereospecific rearrangement of α-ketol 21 to difluoroalkoxyborane 22.

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Figure 7: In the presence of a gold catalyst and water in 1,4-dioxane, 1-alkynylbutanol derivatives undergo t...

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Figure 8: The diastereospecific α-ketol rearrangement of 32 to 33, part of the total synthesis of periconiano...

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Figure 9: Two α-ketol rearrangements, one catalyzed by silica gel on 38 and the other by NaOMe on both 38 and ...

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Figure 10: α-Ketol rearrangement of triumphalone (41) to isotriumphalone (42) via ring contraction.

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Figure 11: Tandem reaction of strophasterol A synthetic intermediate 43 to 44 through a vinylogous α-ketol rea...

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Figure 12: Tandem reaction consisting of a Diels–Alder cycloaddition followed by an α-ketol rearrangement, par...

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Figure 13: Single-pot reaction consisting of Claisen and α-ketol rearrangements, part of the total synthesis o...

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Figure 14: Enzyme-catalyzed α-ketol rearrangements. a) Ketol-acid reductoisomerase (KAR) catalyzes the rearran...

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Figure 15: The conversion of asperfloroid (73) to asperflotone (72), featuring the ring-expanding α-ketol rear...

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Figure 16: Hypothetical interconversion of natural products prekinamycin (76) and isoprekinamycin (77) and che...

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Figure 17: Proposed biosynthetic pathway converting acylphloroglucinol (87) to isolated elodeoidins A–H 92–96....

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Figure 18: α-Iminol rearrangements catalyzed by VANOL Zr (99). The rearrangement can be conducted with preform...

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Figure 19: α-Iminol rearrangements catalyzed by silica gel and montmorillonite K 10. a) For 102a (102 with R =...

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Figure 20: Synthesis of tryptamines 110 via a ring-contracting α‑iminol rearrangement. A mechanism for the fin...

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Figure 21: Tandem synthesis of functionalized α-amino cyclopentanones 119 from heteroarenes 115 and cyclobutan...

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Figure 22: Four eburnane-type alkaloid natural products 122–125 were synthesized from common intermediate 127,...

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Review

Published 15 Oct 2021

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