Asymmetric One-Pot Conjugate Addition of Grignard Reagents to
alpha,beta-Unsaturated Compounds Followed by Reaction with
Carbenium Ions

J 2015

Asymmetric One-Pot Conjugate Addition of Grignard Reagents to alpha,beta-Unsaturated Compounds Followed by Reaction with Carbenium Ions

DRUSAN, Michal, Erik RAKOVSKÝ, Jaromír MAREK a Radovan ŠEBESTA

Základní údaje

Originální název

Asymmetric One-Pot Conjugate Addition of Grignard Reagents to alpha,beta-Unsaturated Compounds Followed by Reaction with Carbenium Ions

Autoři

DRUSAN, Michal (703 Slovensko), Erik RAKOVSKÝ (703 Slovensko), Jaromír MAREK (203 Česká republika, garant, domácí) a Radovan ŠEBESTA (703 Slovensko)

Vydání

ADVANCED SYNTHESIS & CATALYSIS, WEINHEIM, WILEY-V C H VERLAG GMBH, 2015, 1615-4150

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 6.453

Kód RIV

RIV/00216224:14740/15:00084552

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1002/adsc.201500074

UT WoS

000354253600018

Klíčová slova anglicky

asymmetric catalysis; carbocations; conjugate addition; domino reactions; ferrocene ligands

Štítky

CF SAXS, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 1. 4. 2016 15:15, Mgr. Eva Špillingová

Anotace

V originále

Asymmetric catalytic multistep reactions enable the formation of structurally complex compounds from simple starting materials. Enantioselective Cu-catalyzed 1,4-additions of Grignard reagents to Michael acceptors form reactive chiral enolates. We show here that these chiral enolates react in a one-pot fashion with naked carbenium ions, such as tropylium, 1,3-benzodithiolium, and dianisylmethylium ions. The corresponding products were obtained in good yields, with enantioselectivities up to 96% ee and high diastereomeric purities.

Návaznosti

LM2011020, projekt VaV

Název: CEITEC ? open access

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CEITEC - open access

Citovat

DRUSAN, Michal, Erik RAKOVSKÝ, Jaromír MAREK a Radovan ŠEBESTA. Asymmetric One-Pot Conjugate Addition of Grignard Reagents to alpha,beta-Unsaturated Compounds Followed by Reaction with Carbenium Ions. ADVANCED SYNTHESIS & CATALYSIS. WEINHEIM: WILEY-V C H VERLAG GMBH, 2015, roč. 357, č. 7, s. 1493-1498. ISSN 1615-4150. Dostupné z: https://dx.doi.org/10.1002/adsc.201500074.

@article{1316105,
   author = {Drusan, Michal and Rakovský, Erik and Marek, Jaromír and Šebesta, Radovan},
   article_location = {WEINHEIM},
   article_number = {7},
   doi = {http://dx.doi.org/10.1002/adsc.201500074},
   keywords = {asymmetric catalysis; carbocations; conjugate addition; domino reactions; ferrocene ligands},
   language = {eng},
   issn = {1615-4150},
   journal = {ADVANCED SYNTHESIS & CATALYSIS},
   title = {Asymmetric One-Pot Conjugate Addition of Grignard Reagents to alpha,beta-Unsaturated Compounds Followed by Reaction with Carbenium Ions},
   url = {http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500074/abstract;jsessionid=6039F4AD8F14C5AFBD11F8B684CAF703.f03t04},
   volume = {357},
   year = {2015}
}

TY  - JOUR
ID  - 1316105
AU  - Drusan, Michal - Rakovský, Erik - Marek, Jaromír - Šebesta, Radovan
PY  - 2015
TI  - Asymmetric One-Pot Conjugate Addition of Grignard Reagents to alpha,beta-Unsaturated Compounds Followed by Reaction with Carbenium Ions
JF  - ADVANCED SYNTHESIS & CATALYSIS
VL  - 357
IS  - 7
SP  - 1493-1498
EP  - 1493-1498
PB  - WILEY-V C H VERLAG GMBH
SN  - 16154150
KW  - asymmetric catalysis
KW  - carbocations
KW  - conjugate addition
KW  - domino reactions
KW  - ferrocene ligands
UR  - http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500074/abstract;jsessionid=6039F4AD8F14C5AFBD11F8B684CAF703.f03t04
L2  - http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500074/abstract;jsessionid=6039F4AD8F14C5AFBD11F8B684CAF703.f03t04
N2  - Asymmetric catalytic multistep reactions enable the formation of structurally complex compounds from simple starting materials. Enantioselective Cu-catalyzed 1,4-additions of Grignard reagents to Michael acceptors form reactive chiral enolates. We show here that these chiral enolates react in a one-pot fashion with naked carbenium ions, such as tropylium, 1,3-benzodithiolium, and dianisylmethylium ions. The corresponding products were obtained in good yields, with enantioselectivities up to 96% ee and high diastereomeric purities.
ER  -

DRUSAN, Michal, Erik RAKOVSKÝ, Jaromír MAREK a Radovan ŠEBESTA. Asymmetric One-Pot Conjugate Addition of Grignard Reagents to alpha,beta-Unsaturated Compounds Followed by Reaction with Carbenium Ions. \textit{ADVANCED SYNTHESIS \&{} CATALYSIS}. WEINHEIM: WILEY-V C H VERLAG GMBH, 2015, roč.~357, č.~7, s.~1493-1498. ISSN~1615-4150. Dostupné z: https://dx.doi.org/10.1002/adsc.201500074.

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