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

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

54 Citations (Scopus)

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.

Original language	English
Pages (from-to)	18737-18741
Number of pages	5
Journal	Chemistry - A European Journal
Volume	22
Issue number	52
DOIs	https://doi.org/10.1002/chem.201604782
Publication status	Published - 23 Dec 2016
Externally published	Yes

Keywords

alkenes
gem-silylborylation
insertion
iododesilylation
tamoxifen

Access to Document

10.1002/chem.201604782

Cite this

@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 = "John Wiley and Sons Inc",

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 - https://www.scopus.com/pages/publications/85000788281

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this