Palladium-Catalyzed Cascade to Benzoxepins by Using Vinyl-Substituted Donor-Acceptor Cyclopropanes

M. Faltracco; K.N.A. van de Vrande; M. Dijkstra; J.M. Saya; T.A. Hamlin; E. Ruijter

doi:10.1002/anie.202102862

Palladium-Catalyzed Cascade to Benzoxepins by Using Vinyl-Substituted Donor-Acceptor Cyclopropanes

M. Faltracco, K.N.A. van de Vrande, M. Dijkstra, J.M. Saya, T.A. Hamlin, E. Ruijter^*

^*Corresponding author for this work

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

24 Citations (Web of Science)

Abstract

A palladium-catalyzed intermolecular cascade (4+3) cyclocondensation of salicylaldehydes and vinylcyclopropanes is reported. A key feature of the reaction is the use of a phosphonate group as an acceptor moiety on the cyclopropane, exploiting its propensity to undergo olefination with aldehydes. Subsequent O-allylation enabled the formation of a range of substituted benzoxepinsWith a novel chiral ligand, the products were obtained in generally good yield and with reasonable enantioselectivity.

Original language	English
Pages (from-to)	14410-14414
Number of pages	5
Journal	Angewandte Chemie-International Edition
Volume	60
Issue number	26
DOIs	https://doi.org/10.1002/anie.202102862
Publication status	Published - 21 Jun 2021

Keywords

benzoxepins
cascade reactions
olefination
palladium
seven-membered rings
DEAROMATIVE 3+2 CYCLOADDITION
VINYLCYCLOPROPANES
DERIVATIVES
ESTERS
CONSTRUCTION
CARBOCYCLES
LACTONES
ACCESS
AGENTS
ACID

Access to Document

10.1002/anie.202102862Licence: CC BY-NC-ND

Cite this

@article{6741fa791cc04701b66c7af8c2fe22b2,

title = "Palladium-Catalyzed Cascade to Benzoxepins by Using Vinyl-Substituted Donor-Acceptor Cyclopropanes",

abstract = "A palladium-catalyzed intermolecular cascade (4+3) cyclocondensation of salicylaldehydes and vinylcyclopropanes is reported. A key feature of the reaction is the use of a phosphonate group as an acceptor moiety on the cyclopropane, exploiting its propensity to undergo olefination with aldehydes. Subsequent O-allylation enabled the formation of a range of substituted benzoxepinsWith a novel chiral ligand, the products were obtained in generally good yield and with reasonable enantioselectivity.",

keywords = "benzoxepins, cascade reactions, olefination, palladium, seven-membered rings, DEAROMATIVE 3+2 CYCLOADDITION, VINYLCYCLOPROPANES, DERIVATIVES, ESTERS, CONSTRUCTION, CARBOCYCLES, LACTONES, ACCESS, AGENTS, ACID",

author = "M. Faltracco and {van de Vrande}, K.N.A. and M. Dijkstra and J.M. Saya and T.A. Hamlin and E. Ruijter",

year = "2021",

month = jun,

day = "21",

doi = "10.1002/anie.202102862",

language = "English",

volume = "60",

pages = "14410--14414",

journal = "Angewandte Chemie-International Edition",

issn = "1433-7851",

publisher = "Wiley-VCH Verlag",

number = "26",

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TY - JOUR

T1 - Palladium-Catalyzed Cascade to Benzoxepins by Using Vinyl-Substituted Donor-Acceptor Cyclopropanes

AU - Faltracco, M.

AU - van de Vrande, K.N.A.

AU - Dijkstra, M.

AU - Saya, J.M.

AU - Hamlin, T.A.

AU - Ruijter, E.

PY - 2021/6/21

Y1 - 2021/6/21

N2 - A palladium-catalyzed intermolecular cascade (4+3) cyclocondensation of salicylaldehydes and vinylcyclopropanes is reported. A key feature of the reaction is the use of a phosphonate group as an acceptor moiety on the cyclopropane, exploiting its propensity to undergo olefination with aldehydes. Subsequent O-allylation enabled the formation of a range of substituted benzoxepinsWith a novel chiral ligand, the products were obtained in generally good yield and with reasonable enantioselectivity.

AB - A palladium-catalyzed intermolecular cascade (4+3) cyclocondensation of salicylaldehydes and vinylcyclopropanes is reported. A key feature of the reaction is the use of a phosphonate group as an acceptor moiety on the cyclopropane, exploiting its propensity to undergo olefination with aldehydes. Subsequent O-allylation enabled the formation of a range of substituted benzoxepinsWith a novel chiral ligand, the products were obtained in generally good yield and with reasonable enantioselectivity.

KW - benzoxepins

KW - cascade reactions

KW - olefination

KW - palladium

KW - seven-membered rings

KW - DEAROMATIVE 3+2 CYCLOADDITION

KW - VINYLCYCLOPROPANES

KW - DERIVATIVES

KW - ESTERS

KW - CONSTRUCTION

KW - CARBOCYCLES

KW - LACTONES

KW - ACCESS

KW - AGENTS

KW - ACID

U2 - 10.1002/anie.202102862

DO - 10.1002/anie.202102862

M3 - Article

C2 - 33822456

SN - 1433-7851

VL - 60

SP - 14410

EP - 14414

JO - Angewandte Chemie-International Edition

JF - Angewandte Chemie-International Edition

IS - 26

ER -