Opportune gem-Silylborylation of Carbonyl Compounds: A Modular and Stereocontrolled Entry to Tetrasubstituted Olefins

Enrico La Cascia; Ana B. Cuenca; Elena Fernández

doi:10.1002/chem.201604782

Opportune gem-Silylborylation of Carbonyl Compounds: A Modular and Stereocontrolled Entry to Tetrasubstituted Olefins

Enrico La Cascia, Ana B. Cuenca, Elena Fernández

Producció científica: Article en revista indexada › Article › Avaluat per experts

49 Cites (Scopus)

Resum

An easy access to highly versatile gem-silylboronate synthons is achieved by means of a new olefination reagent, HC(Bpin)₂(SiMe₃). Subsequent silicon or boron-based selective functionalization allows for the modular and stereocontrolled synthesis of all-carbon tetrasubstituted alkenes. A particular attraction of this approach is the iododesilylation reaction, which becomes a pivotal tool for C−Si functionalization.

Idioma original	Anglès
Pàgines (de-a)	18737-18741
Nombre de pàgines	5
Revista	Chemistry - A European Journal
Volum	22
Número	52
DOIs	https://doi.org/10.1002/chem.201604782
Estat de la publicació	Publicada - 23 de des. 2016
Publicat externament	Sí

Accés al document

10.1002/chem.201604782

Altres arxius i enllaços

Com citar-ho

@article{1a558821595748818070046472212484,

title = "Opportune gem-Silylborylation of Carbonyl Compounds: A Modular and Stereocontrolled Entry to Tetrasubstituted Olefins",

abstract = "An easy access to highly versatile gem-silylboronate synthons is achieved by means of a new olefination reagent, HC(Bpin)2(SiMe3). Subsequent silicon or boron-based selective functionalization allows for the modular and stereocontrolled synthesis of all-carbon tetrasubstituted alkenes. A particular attraction of this approach is the iododesilylation reaction, which becomes a pivotal tool for C−Si functionalization.",

keywords = "alkenes, gem-silylborylation, insertion, iododesilylation, tamoxifen",

author = "{La Cascia}, Enrico and Cuenca, {Ana B.} and Elena Fern{\'a}ndez",

note = "Publisher Copyright: {\textcopyright} 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

month = dec,

day = "23",

doi = "10.1002/chem.201604782",

language = "English",

volume = "22",

pages = "18737--18741",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "52",

}

TY - JOUR

T1 - Opportune gem-Silylborylation of Carbonyl Compounds

T2 - A Modular and Stereocontrolled Entry to Tetrasubstituted Olefins

AU - La Cascia, Enrico

AU - Cuenca, Ana B.

AU - Fernández, Elena

PY - 2016/12/23

Y1 - 2016/12/23

N2 - An easy access to highly versatile gem-silylboronate synthons is achieved by means of a new olefination reagent, HC(Bpin)2(SiMe3). Subsequent silicon or boron-based selective functionalization allows for the modular and stereocontrolled synthesis of all-carbon tetrasubstituted alkenes. A particular attraction of this approach is the iododesilylation reaction, which becomes a pivotal tool for C−Si functionalization.

AB - An easy access to highly versatile gem-silylboronate synthons is achieved by means of a new olefination reagent, HC(Bpin)2(SiMe3). Subsequent silicon or boron-based selective functionalization allows for the modular and stereocontrolled synthesis of all-carbon tetrasubstituted alkenes. A particular attraction of this approach is the iododesilylation reaction, which becomes a pivotal tool for C−Si functionalization.

KW - alkenes

KW - gem-silylborylation

KW - insertion

KW - iododesilylation

KW - tamoxifen

UR - http://www.scopus.com/inward/record.url?scp=85000788281&partnerID=8YFLogxK

UR - https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=pure_univeritat_ramon_llull&SrcAuth=WosAPI&KeyUT=WOS:000393219300015&DestLinkType=FullRecord&DestApp=WOS_CPL

U2 - 10.1002/chem.201604782

DO - 10.1002/chem.201604782

M3 - Article

C2 - 27735083

AN - SCOPUS:85000788281

SN - 0947-6539

VL - 22

SP - 18737

EP - 18741

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 52

ER -

Opportune gem-Silylborylation of Carbonyl Compounds: A Modular and Stereocontrolled Entry to Tetrasubstituted Olefins

Resum

Accés al document

Altres arxius i enllaços

Fingerprint

Com citar-ho