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 and Radovan ŠEBESTA

Basic information

Original name

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

Authors

DRUSAN, Michal (703 Slovakia), Erik RAKOVSKÝ (703 Slovakia), Jaromír MAREK (203 Czech Republic, guarantor, belonging to the institution) and Radovan ŠEBESTA (703 Slovakia)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 6.453

RIV identification code

RIV/00216224:14740/15:00084552

Organization unit

Central European Institute of Technology

DOI

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

UT WoS

000354253600018

Keywords in English

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

Abstract

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.

Links

LM2011020, research and development project

Name: CEITEC ? open access

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

DRUSAN, Michal, Erik RAKOVSKÝ, Jaromír MAREK and 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, vol. 357, No 7, p. 1493-1498. ISSN 1615-4150. Available from: 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 and 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, vol.~357, No~7, p.~1493-1498. ISSN~1615-4150. Available from: https://dx.doi.org/10.1002/adsc.201500074.

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