A Rare Alder-ene Cycloisomerization of 1,6-Allenynes

Liam M. Joyce; Melanie A. Drew; Andrew J. Tague; Thanaphat Thaima; Ali Gouranourimi; Alireza Ariafard; Stephen G. Pyne; Christopher J.T. Hyland

doi:10.1002/chem.202104022

A Rare Alder-ene Cycloisomerization of 1,6-Allenynes

Liam M. Joyce
, Melanie A. Drew
, Andrew J. Tague
, Thanaphat Thaima
, Ali Gouranourimi
, Alireza Ariafard^*
, Stephen G. Pyne^*
, Christopher J.T. Hyland^*

^*Corresponding author for this work

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

7 Citations (Scopus)

Abstract

Thermally induced cycloisomerization reactions of 1,6-allenynes gives α-methylene-γ-lactams via intramolecular Alder-ene reactions. The mechanism is supported by computational and deuterium labelling studies. This thermal, non-radical method enables the discovery of a hitherto unknown route that proceeds via a divergent mechanism distinct from the previous [2+2] cycloisomerization manifold.

Original language	English
Article number	e202104022
Number of pages	5
Journal	Chemistry - A European Journal
Volume	28
Issue number	12
Early online date	21 Dec 2021
DOIs	https://doi.org/10.1002/chem.202104022
Publication status	Published - 24 Feb 2022
Externally published	Yes

Access to Document

10.1002/chem.202104022

Cite this

@article{3b6059ccecda424888a983bc080fa515,

title = "A Rare Alder-ene Cycloisomerization of 1,6-Allenynes",

abstract = "Thermally induced cycloisomerization reactions of 1,6-allenynes gives α-methylene-γ-lactams via intramolecular Alder-ene reactions. The mechanism is supported by computational and deuterium labelling studies. This thermal, non-radical method enables the discovery of a hitherto unknown route that proceeds via a divergent mechanism distinct from the previous [2+2] cycloisomerization manifold.",

keywords = "1,6-allenyne, Alder-ene, computations, cycloisomerization, lactam",

author = "Joyce, \{Liam M.\} and Drew, \{Melanie A.\} and Tague, \{Andrew J.\} and Thanaphat Thaima and Ali Gouranourimi and Alireza Ariafard and Pyne, \{Stephen G.\} and Hyland, \{Christopher J.T.\}",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH.",

year = "2022",

month = feb,

day = "24",

doi = "10.1002/chem.202104022",

language = "English",

volume = "28",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag GmbH",

number = "12",

}

TY - JOUR

T1 - A Rare Alder-ene Cycloisomerization of 1,6-Allenynes

AU - Joyce, Liam M.

AU - Drew, Melanie A.

AU - Tague, Andrew J.

AU - Thaima, Thanaphat

AU - Gouranourimi, Ali

AU - Ariafard, Alireza

AU - Pyne, Stephen G.

AU - Hyland, Christopher J.T.

PY - 2022/2/24

Y1 - 2022/2/24

N2 - Thermally induced cycloisomerization reactions of 1,6-allenynes gives α-methylene-γ-lactams via intramolecular Alder-ene reactions. The mechanism is supported by computational and deuterium labelling studies. This thermal, non-radical method enables the discovery of a hitherto unknown route that proceeds via a divergent mechanism distinct from the previous [2+2] cycloisomerization manifold.

AB - Thermally induced cycloisomerization reactions of 1,6-allenynes gives α-methylene-γ-lactams via intramolecular Alder-ene reactions. The mechanism is supported by computational and deuterium labelling studies. This thermal, non-radical method enables the discovery of a hitherto unknown route that proceeds via a divergent mechanism distinct from the previous [2+2] cycloisomerization manifold.

KW - 1,6-allenyne

KW - Alder-ene

KW - computations

KW - cycloisomerization

KW - lactam

UR - https://www.scopus.com/pages/publications/85123908278

U2 - 10.1002/chem.202104022

DO - 10.1002/chem.202104022

M3 - Article

C2 - 34971450

AN - SCOPUS:85123908278

SN - 0947-6539

VL - 28

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 12

M1 - e202104022

ER -

A Rare Alder-ene Cycloisomerization of 1,6-Allenynes

Abstract

Access to Document

Other files and links

Fingerprint

Cite this