TY - JOUR
T1 - Cycloaddition Initiated by Ynolates
T2 - High-Energy Dianion Equivalents as a Molecular Glue
AU - Shindo, Mitsuru
AU - Iwata, Takayuki
N1 - Funding Information:
Financial support was provided by the Japan Society for the Promotion of Science (JSPS KAKENHI; grant no. JP18H02557, JP18H04418, JP18H04624, JP20H04780, JP20K21198, and JP20K15283), NAGASE Science Technology Foundation (M.S.), Asahi Glass Foundation (T.I.), Qdai-jump Research Program Wakaba Challenge at Kyushu University (T.I.), and the IRCCS Fusion Emergent Research Program (T.I.).JapaSoiettfPhyooermotioScien(ceJP18H02557JapaSociehPoreomotioSoncfien(ceJP18H04418JapaSociefhyoPeomotSoocnfien(ceJP18H04624)JapaSnocihePyomotoSocnifenceJP20H04780)JapaSnocihePeyormoiooScfien(ceJP20K21198JapaSociehtfPyoreomotioSoncfien(ceJP20K15283)NagSasceienTcechnoloFgoyundationAahGil FoasusndationKyushUniveity
Publisher Copyright:
© 2022 Georg Thieme Verlag. All rights reserved.
PY - 2022/4/1
Y1 - 2022/4/1
N2 - In this paper, ynolate-initiated cycloaddition (annulation) to form a range of carbocycles and heterocycles is described. Ynolates consist of a ketene anion equivalent, which contains both nucleophilic and electrophilic moieties, and a carbodianion equivalent that achieves double addition. Hence, in addition to the usual [n+2] cycloaddition, ynolates can perform formal [n+1]-type annulations. Their high-energy performance has been demonstrated by their triple addition to arynes to generate triptycenes, in which the C?C triple bond of ynolates is cleaved. The synthetic applications of these methods, including natural products synthesis, are also described.
AB - In this paper, ynolate-initiated cycloaddition (annulation) to form a range of carbocycles and heterocycles is described. Ynolates consist of a ketene anion equivalent, which contains both nucleophilic and electrophilic moieties, and a carbodianion equivalent that achieves double addition. Hence, in addition to the usual [n+2] cycloaddition, ynolates can perform formal [n+1]-type annulations. Their high-energy performance has been demonstrated by their triple addition to arynes to generate triptycenes, in which the C?C triple bond of ynolates is cleaved. The synthetic applications of these methods, including natural products synthesis, are also described.
UR - http://www.scopus.com/inward/record.url?scp=85120328784&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85120328784&partnerID=8YFLogxK
U2 - 10.1055/s-0040-1719857
DO - 10.1055/s-0040-1719857
M3 - Article
AN - SCOPUS:85120328784
SN - 0936-5214
VL - 33
SP - 531
EP - 545
JO - Synlett
JF - Synlett
IS - 6
ER -