Rh(II)-Catalyzed spirocyclization of α-diazo homophthalimides with cyclic ethers

Standard

Rh(II)-Catalyzed spirocyclization of α-diazo homophthalimides with cyclic ethers. / Guranova, Natalia I.; Dar’in, Dmitry ; Kantin, Grigory ; Novikov, Alexander S.; Bakulina, Olga ; Krasavin, Mikhail.

In: The Journal of organic chemistry, Vol. 84, No. 7, 05.04.2019, p. 4534-4542.

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

BibTeX

@article{2e08f40eb6244e219a27443e5df9d38b,

title = "Rh(II)-Catalyzed spirocyclization of α-diazo homophthalimides with cyclic ethers",

abstract = "Rh(II)-catalyzed decomposition of α-diazo homophthalimides in the presence of cyclic ethers gave spirocyclic products of Stevens-type [1,2]-alkyl shift within the postulated oxonium ylide intermediate. Such a reaction pathway is in line with thermodynamic predictions obtained from quantum chemical calculations performed at the B3LYP/6-31G∗ and B3LYP/6-311++G∗∗ levels of theory. These findings represent the first systematically investigated case of spirocyclization of cyclic α-diazocarbonyl compounds with cyclic ethers.",

keywords = "CARBENOID MEDIATED CYCLIZATIONS, BETA-KETO-ESTERS, DIASTEREOSELECTIVE SYNTHESIS, RING EXPANSION, OXONIUM, DERIVATIVES, YLIDES, MACROCYCLIZATION, DECOMPOSITION, HETEROCYCLES",

author = "Guranova, {Natalia I.} and Dmitry Dar{\textquoteright}in and Grigory Kantin and Novikov, {Alexander S.} and Olga Bakulina and Mikhail Krasavin",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = apr,

day = "5",

doi = "10.1021/acs.joc.9b00245",

language = "English",

volume = "84",

pages = "4534--4542",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "7",

}

RIS

TY - JOUR

T1 - Rh(II)-Catalyzed spirocyclization of α-diazo homophthalimides with cyclic ethers

AU - Guranova, Natalia I.

AU - Dar’in, Dmitry

AU - Kantin, Grigory

AU - Novikov, Alexander S.

AU - Bakulina, Olga

AU - Krasavin, Mikhail

PY - 2019/4/5

Y1 - 2019/4/5

N2 - Rh(II)-catalyzed decomposition of α-diazo homophthalimides in the presence of cyclic ethers gave spirocyclic products of Stevens-type [1,2]-alkyl shift within the postulated oxonium ylide intermediate. Such a reaction pathway is in line with thermodynamic predictions obtained from quantum chemical calculations performed at the B3LYP/6-31G∗ and B3LYP/6-311++G∗∗ levels of theory. These findings represent the first systematically investigated case of spirocyclization of cyclic α-diazocarbonyl compounds with cyclic ethers.

AB - Rh(II)-catalyzed decomposition of α-diazo homophthalimides in the presence of cyclic ethers gave spirocyclic products of Stevens-type [1,2]-alkyl shift within the postulated oxonium ylide intermediate. Such a reaction pathway is in line with thermodynamic predictions obtained from quantum chemical calculations performed at the B3LYP/6-31G∗ and B3LYP/6-311++G∗∗ levels of theory. These findings represent the first systematically investigated case of spirocyclization of cyclic α-diazocarbonyl compounds with cyclic ethers.

KW - CARBENOID MEDIATED CYCLIZATIONS

KW - BETA-KETO-ESTERS

KW - DIASTEREOSELECTIVE SYNTHESIS

KW - RING EXPANSION

KW - OXONIUM

KW - DERIVATIVES

KW - YLIDES

KW - MACROCYCLIZATION

KW - DECOMPOSITION

KW - HETEROCYCLES

UR - http://www.scopus.com/inward/record.url?scp=85063950407&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/rhiicatalyzed-spirocyclization-%CE%B1diazo-homophthalimides-cyclic-ethers

U2 - 10.1021/acs.joc.9b00245

DO - 10.1021/acs.joc.9b00245

M3 - Article

C2 - 30816715

VL - 84

SP - 4534

EP - 4542

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 7

ER -

ID: 39842098