Journal of Organic Chemistry

, volume 83 , issue 4 , pages 2293-2308

(R)-DM-SEGPHOS–Ag(I)-Catalyzed Enantioselective Synthesis of Pyrrolidines and Pyrrolizidines via (1,3)- and Double (1,3)-Dipolar Cycloaddition Reactions

Sumit K Ray ¹

Rayhan G Biswas ¹

Arun Suneja ¹

Milon M Sadhu ¹

Rybnikova Z.P. ^{1, 2}

Hide authors affiliations Show authors affiliations: 2 affiliations

Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal, Madhya Pradesh 462 066, India |

Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, Uttar Pradesh 208 016, India |

Publication type: Journal Article

Publication date: 2018-02-01

American Chemical Society (ACS)

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.7b03185

Copy DOI

PubMed ID: 29364672

Organic Chemistry

Abstract

An efficient diastereo- and enantioselective route to access a wide range of highly substituted pyrrolidine and pyrrolizidine derivatives has been described via (1,3)- and double (1,3)-dipolar cycloaddition reactions catalyzed by the (R)-DM-SEGPHOS-Ag(I) complex. The reactions proceed smoothly at ambient temperature, affording a variety of pyrrolidines and pyrrolizidines in high yields (up to 93%) with up to 99:1 dr and excellent enantioselectivities (up to 98% ee) without any additives. The newly synthesized pyrrolidine and pyrrolizidine derivatives contain four and seven contiguous stereogenic centers, respectively. Moreover, the synthetic utility of enantioenriched products has been demonstrated by transforming them into various synthetically useful advanced intermediates.

Found

2 citations

Gazizov Almir

🥼

DSc in Chemistry

157 publications, 895 citations, 23 reviews

h-index: 14

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

Research interests

Heterocyclic compounds

Organic Chemistry

Organophosphorus chemistry

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GOST |

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Ray S. K. et al. (R)-DM-SEGPHOS–Ag(I)-Catalyzed Enantioselective Synthesis of Pyrrolidines and Pyrrolizidines via (1,3)- and Double (1,3)-Dipolar Cycloaddition Reactions // Journal of Organic Chemistry. 2018. Vol. 83. No. 4. pp. 2293-2308.

GOST all authors (up to 50) Copy

Ray S. K., Biswas R. G., Suneja A., Sadhu M. M., Z.P. R. (R)-DM-SEGPHOS–Ag(I)-Catalyzed Enantioselective Synthesis of Pyrrolidines and Pyrrolizidines via (1,3)- and Double (1,3)-Dipolar Cycloaddition Reactions // Journal of Organic Chemistry. 2018. Vol. 83. No. 4. pp. 2293-2308.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.joc.7b03185

UR - https://doi.org/10.1021/acs.joc.7b03185

TI - (R)-DM-SEGPHOS–Ag(I)-Catalyzed Enantioselective Synthesis of Pyrrolidines and Pyrrolizidines via (1,3)- and Double (1,3)-Dipolar Cycloaddition Reactions

T2 - Journal of Organic Chemistry

AU - Ray, Sumit K

AU - Biswas, Rayhan G

AU - Suneja, Arun

AU - Sadhu, Milon M

AU - Z.P., Rybnikova

PY - 2018

DA - 2018/02/01

PB - American Chemical Society (ACS)

SP - 2293-2308

IS - 4

VL - 83

PMID - 29364672

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2018_Ray,

author = {Sumit K Ray and Rayhan G Biswas and Arun Suneja and Milon M Sadhu and Rybnikova Z.P.},

title = {(R)-DM-SEGPHOS–Ag(I)-Catalyzed Enantioselective Synthesis of Pyrrolidines and Pyrrolizidines via (1,3)- and Double (1,3)-Dipolar Cycloaddition Reactions},

journal = {Journal of Organic Chemistry},

year = {2018},

volume = {83},

publisher = {American Chemical Society (ACS)},

month = {feb},

url = {https://doi.org/10.1021/acs.joc.7b03185},

number = {4},

pages = {2293--2308},

doi = {10.1021/acs.joc.7b03185}

}

MLA

Cite this

MLA Copy

Ray, Sumit K., et al. “(R)-DM-SEGPHOS–Ag(I)-Catalyzed Enantioselective Synthesis of Pyrrolidines and Pyrrolizidines via (1,3)- and Double (1,3)-Dipolar Cycloaddition Reactions.” Journal of Organic Chemistry, vol. 83, no. 4, Feb. 2018, pp. 2293-2308. https://doi.org/10.1021/acs.joc.7b03185.

Publisher

American Chemical Society (ACS)

Journal

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR

0.737

CiteScore

6.1

Impact factor

3.6

ISSN

00223263 (Print)

15206904 (Electronic)

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