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Three-Component Reaction of Homophthalic Anhydride with Carbonyl Compounds and Ammonium Acetate : New Developments. / Safrygin, Alexander; Bakulina, Olga; Dar'In, Dmitry; Krasavin, Mikhail.

In: Synthesis (Germany), Vol. 52, No. 15, 04.08.2020, p. 2190-2195.

Research output: Contribution to journal › Article › peer-review

Harvard

Safrygin, A, Bakulina, O, Dar'In, D & Krasavin, M 2020, 'Three-Component Reaction of Homophthalic Anhydride with Carbonyl Compounds and Ammonium Acetate: New Developments', Synthesis (Germany), vol. 52, no. 15, pp. 2190-2195. https://doi.org/10.1055/s-0040-1708017

APA

Safrygin, A., Bakulina, O., Dar'In, D., & Krasavin, M. (2020). Three-Component Reaction of Homophthalic Anhydride with Carbonyl Compounds and Ammonium Acetate: New Developments. Synthesis (Germany), 52(15), 2190-2195. https://doi.org/10.1055/s-0040-1708017

Vancouver

Safrygin A, Bakulina O, Dar'In D, Krasavin M. Three-Component Reaction of Homophthalic Anhydride with Carbonyl Compounds and Ammonium Acetate: New Developments. Synthesis (Germany). 2020 Aug 4;52(15):2190-2195. https://doi.org/10.1055/s-0040-1708017

Author

Safrygin, Alexander ; Bakulina, Olga ; Dar'In, Dmitry ; Krasavin, Mikhail. / Three-Component Reaction of Homophthalic Anhydride with Carbonyl Compounds and Ammonium Acetate : New Developments. In: Synthesis (Germany). 2020 ; Vol. 52, No. 15. pp. 2190-2195.

BibTeX

@article{75a77d685da34edc87a3b2df3acb8baf,
title = "Three-Component Reaction of Homophthalic Anhydride with Carbonyl Compounds and Ammonium Acetate: New Developments",
abstract = "The earlier described reaction of homophthalic anhydrides with aromatic ketones and ammonium acetate was tested for cyclic ketones (yielding spirocyclic motifs) and aliphatic aldehydes. In contrast to previous findings, the reaction was found to require no catalyst at all and to be applicable, in the non-catalyzed format, to these new carbonyl substrates as well as aromatic ketones. The reaction typically proceeds with high diastereoselectivity; if not, the initial diastereomeric mixture can be quantitatively equilibrated into a single, trans-diastereomer on treatment with aqueous base.",
keywords = "Castagnoli-Cushman reaction, catalyst-free, dia-stereoselectivity, homophthalic anhydride, spirocyclic compounds, tetrahydroisoquinolonic acids",
author = "Alexander Safrygin and Olga Bakulina and Dmitry Dar'In and Mikhail Krasavin",
year = "2020",
month = aug,
day = "4",
doi = "10.1055/s-0040-1708017",
language = "English",
volume = "52",
pages = "2190--2195",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "15",

}

RIS

TY - JOUR

T1 - Three-Component Reaction of Homophthalic Anhydride with Carbonyl Compounds and Ammonium Acetate

T2 - New Developments

AU - Safrygin, Alexander

AU - Bakulina, Olga

AU - Dar'In, Dmitry

AU - Krasavin, Mikhail

PY - 2020/8/4

Y1 - 2020/8/4

N2 - The earlier described reaction of homophthalic anhydrides with aromatic ketones and ammonium acetate was tested for cyclic ketones (yielding spirocyclic motifs) and aliphatic aldehydes. In contrast to previous findings, the reaction was found to require no catalyst at all and to be applicable, in the non-catalyzed format, to these new carbonyl substrates as well as aromatic ketones. The reaction typically proceeds with high diastereoselectivity; if not, the initial diastereomeric mixture can be quantitatively equilibrated into a single, trans-diastereomer on treatment with aqueous base.

AB - The earlier described reaction of homophthalic anhydrides with aromatic ketones and ammonium acetate was tested for cyclic ketones (yielding spirocyclic motifs) and aliphatic aldehydes. In contrast to previous findings, the reaction was found to require no catalyst at all and to be applicable, in the non-catalyzed format, to these new carbonyl substrates as well as aromatic ketones. The reaction typically proceeds with high diastereoselectivity; if not, the initial diastereomeric mixture can be quantitatively equilibrated into a single, trans-diastereomer on treatment with aqueous base.

KW - Castagnoli-Cushman reaction

KW - catalyst-free

KW - dia-stereoselectivity

KW - homophthalic anhydride

KW - spirocyclic compounds

KW - tetrahydroisoquinolonic acids

UR - http://www.scopus.com/inward/record.url?scp=85089025547&partnerID=8YFLogxK

U2 - 10.1055/s-0040-1708017

DO - 10.1055/s-0040-1708017

M3 - Article

AN - SCOPUS:85089025547

VL - 52

SP - 2190

EP - 2195

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 15

ER -

ID: 61393637