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1 article(s) from Klychnikov, Mikhail K

α,γ-Dioxygenated amides via tandem Brook rearrangement/radical oxygenation reactions and their application to syntheses of γ-lactams

Mikhail K. Klychnikov,
Radek Pohl,
Ivana Císařová and
Ullrich Jahn

Beilstein J. Org. Chem. 2021, 17, 688–704, doi:10.3762/bjoc.17.58

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Graphical Abstract

Figure 1: Selected alkaloids containing the pyrrolidone motif.

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Scheme 1: A) Classical γ-lactam synthesis by atom transfer radical cyclizations; B) previously developed tand...

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Figure 2: X-ray crystal structure of the major (2R,4S)-alkoxyamine hydrochloride derived from 9j. Displacemen...

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Scheme 2: Formation of the α-(aminoxy)amides 9o,p.

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Figure 3: X-ray crystal structure of the minor cis-diastereomers of the keto lactam 13j (left) and the hydrox...

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Scheme 3: Thermal radical cyclization reactions of amides 9l–p bearing cyclic units. Conditions: a) t-BuOH, 1...

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Scheme 4: Epimerization of spirolactams 12m,n.

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Scheme 5: The Dess–Martin oxidation of lactams 12l–o. Conditions: a) DMP (1.3 equiv), t-BuOH (10 mol %), CH₂Cl...

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Scheme 6: Selected transformations of the lactams trans-12b and 12o.

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Scheme 7: Diastereoselectivity for the formation of α-(aminoxy)amides 9i–k.

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Scheme 8: Rationalization of the diastereoselectivity for the formation of the α-(aminoxy)amide 9l.

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Scheme 9: Rationalization of the thermal radical cyclization diastereoselectivity of alkoxyamines 9a–k. (S)-C...

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Scheme 10: The stereochemical course for the formation of products 12m,n by thermal radical cyclization of alk...

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Scheme 11: Formation of bicycles 12o,p.

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Published 09 Mar 2021

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