An intramolecular oxa-Michael addition on prebuilt β-lactam tethered α, β-unsaturated ester: A remarkable synthesis of a unique scaffold of 2,3-fused β-lactam-1,4-dioxepane

Ram N. Yadav; Armando Paniagua; Bimal K. Banik

doi:10.1016/j.jics.2021.100010

An intramolecular oxa-Michael addition on prebuilt β-lactam tethered α, β-unsaturated ester: A remarkable synthesis of a unique scaffold of 2,3-fused β-lactam-1,4-dioxepane

Ram N. Yadav, Armando Paniagua, Bimal K. Banik

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

Abstract

An expeditious base assisted highly diastereoselective intramolecular oxy-Michael addition reaction in the synthesis of enantiomerically pure 1,4-dioxepane fused β-lactam has been described. This present study has been portrayed a rapid intramolecular 7-exo-trig oxy-Michael reaction involving chemoselective nucleophilic addition of 2⁰ alcohol of the vic-diols to an α β-unsaturated ester. Furthermore, the developed methodology elaborates an extremely atom-economical approach in constructing the C–O bond in stereoselective fashion under mild reaction conditions.

Original language	English
Article number	100010
Journal	Journal of the Indian Chemical Society
Volume	98
Issue number	4
DOIs	https://doi.org/10.1016/j.jics.2021.100010
State	Published - Apr 2021
Externally published	Yes

Keywords

1,4-Dioxepane
B-lactam
Conjugate addition
Diol
Intramolecular
Michael addition reaction
Oxy-Michael reaction
a,b-unsaturated ester

Access to Document

10.1016/j.jics.2021.100010

Cite this

@article{f13a86528f3e445da9c5e68bb198fbce,

title = "An intramolecular oxa-Michael addition on prebuilt β-lactam tethered α, β-unsaturated ester: A remarkable synthesis of a unique scaffold of 2,3-fused β-lactam-1,4-dioxepane",

abstract = "An expeditious base assisted highly diastereoselective intramolecular oxy-Michael addition reaction in the synthesis of enantiomerically pure 1,4-dioxepane fused β-lactam has been described. This present study has been portrayed a rapid intramolecular 7-exo-trig oxy-Michael reaction involving chemoselective nucleophilic addition of 20 alcohol of the vic-diols to an α β-unsaturated ester. Furthermore, the developed methodology elaborates an extremely atom-economical approach in constructing the C–O bond in stereoselective fashion under mild reaction conditions.",

keywords = "1,4-Dioxepane, B-lactam, Conjugate addition, Diol, Intramolecular, Michael addition reaction, Oxy-Michael reaction, a,b-unsaturated ester",

author = "Yadav, {Ram N.} and Armando Paniagua and Banik, {Bimal K.}",

note = "Publisher Copyright: {\textcopyright} 2021 Elsevier B.V.",

year = "2021",

month = apr,

doi = "10.1016/j.jics.2021.100010",

language = "Ingl{\'e}s",

volume = "98",

journal = "Journal of the Indian Chemical Society",

issn = "0019-4522",

number = "4",

}

An intramolecular oxa-Michael addition on prebuilt β-lactam tethered α, β-unsaturated ester: A remarkable synthesis of a unique scaffold of 2,3-fused β-lactam-1,4-dioxepane. / Yadav, Ram N.; Paniagua, Armando; Banik, Bimal K.
In: Journal of the Indian Chemical Society, Vol. 98, No. 4, 100010, 04.2021.

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

TY - JOUR

T1 - An intramolecular oxa-Michael addition on prebuilt β-lactam tethered α, β-unsaturated ester

T2 - A remarkable synthesis of a unique scaffold of 2,3-fused β-lactam-1,4-dioxepane

AU - Yadav, Ram N.

AU - Paniagua, Armando

AU - Banik, Bimal K.

PY - 2021/4

Y1 - 2021/4

N2 - An expeditious base assisted highly diastereoselective intramolecular oxy-Michael addition reaction in the synthesis of enantiomerically pure 1,4-dioxepane fused β-lactam has been described. This present study has been portrayed a rapid intramolecular 7-exo-trig oxy-Michael reaction involving chemoselective nucleophilic addition of 20 alcohol of the vic-diols to an α β-unsaturated ester. Furthermore, the developed methodology elaborates an extremely atom-economical approach in constructing the C–O bond in stereoselective fashion under mild reaction conditions.

AB - An expeditious base assisted highly diastereoselective intramolecular oxy-Michael addition reaction in the synthesis of enantiomerically pure 1,4-dioxepane fused β-lactam has been described. This present study has been portrayed a rapid intramolecular 7-exo-trig oxy-Michael reaction involving chemoselective nucleophilic addition of 20 alcohol of the vic-diols to an α β-unsaturated ester. Furthermore, the developed methodology elaborates an extremely atom-economical approach in constructing the C–O bond in stereoselective fashion under mild reaction conditions.

KW - 1,4-Dioxepane

KW - B-lactam

KW - Conjugate addition

KW - Diol

KW - Intramolecular

KW - Michael addition reaction

KW - Oxy-Michael reaction

KW - a,b-unsaturated ester

UR - http://www.scopus.com/inward/record.url?scp=85108407351&partnerID=8YFLogxK

U2 - 10.1016/j.jics.2021.100010

DO - 10.1016/j.jics.2021.100010

M3 - Artículo

AN - SCOPUS:85108407351

SN - 0019-4522

VL - 98

JO - Journal of the Indian Chemical Society

JF - Journal of the Indian Chemical Society

IS - 4

M1 - 100010

ER -

An intramolecular oxa-Michael addition on prebuilt β-lactam tethered α, β-unsaturated ester: A remarkable synthesis of a unique scaffold of 2,3-fused β-lactam-1,4-dioxepane

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this