Organic Letters

, volume 18 , issue 11 , pages 2632-2635

Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4 + 2]-Annulation Reaction

Adithi Danda ^{1, 2}

Naredla Kesava Reddy ¹

Christopher Golz ²

Carsten Strohmann ²

Kamal Kumar ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Straße 11, 44227 Dortmund, Germany |

Fakultät Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany |

Publication type: Journal Article

Publication date: 2016-05-17

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.6b01030

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PubMed ID: 27187586

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

The catalytic addition of the amino acid derived bifunctional N-acylaminophosphine to an α-substituted allene ester generated a zwitterionic dipole that engaged the vinylogous ester function of 3-cyano-chromones in a [4 + 2] annulation reaction to deliver tetrahydroxanthones embodying three consecutive chiral centers in high yields and with excellent enantioselectivities. The established asymmetric synthesis further paves the way to two different classes of complex, sp(3)-rich tetracyclic benzopyrans via efficient cascade reactions.

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A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

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A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

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North Caucasus Federal University

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Mendeleev University of Chemical Technology of Russia

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Danda A. et al. Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4 + 2]-Annulation Reaction // Organic Letters. 2016. Vol. 18. No. 11. pp. 2632-2635.

GOST all authors (up to 50) Copy

Danda A., Kesava Reddy N., Golz C., Strohmann C., Kumar K. Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4 + 2]-Annulation Reaction // Organic Letters. 2016. Vol. 18. No. 11. pp. 2632-2635.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.6b01030

UR - https://doi.org/10.1021/acs.orglett.6b01030

TI - Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4 + 2]-Annulation Reaction

T2 - Organic Letters

AU - Danda, Adithi

AU - Kesava Reddy, Naredla

AU - Golz, Christopher

AU - Strohmann, Carsten

AU - Kumar, Kamal

PY - 2016

DA - 2016/05/17

PB - American Chemical Society (ACS)

SP - 2632-2635

IS - 11

VL - 18

PMID - 27187586

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2016_Danda,

author = {Adithi Danda and Naredla Kesava Reddy and Christopher Golz and Carsten Strohmann and Kamal Kumar},

title = {Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4 + 2]-Annulation Reaction},

journal = {Organic Letters},

year = {2016},

volume = {18},

publisher = {American Chemical Society (ACS)},

month = {may},

url = {https://doi.org/10.1021/acs.orglett.6b01030},

number = {11},

pages = {2632--2635},

doi = {10.1021/acs.orglett.6b01030}

}

MLA

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MLA Copy

Danda, Adithi, et al. “Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4 + 2]-Annulation Reaction.” Organic Letters, vol. 18, no. 11, May. 2016, pp. 2632-2635. https://doi.org/10.1021/acs.orglett.6b01030.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)