Lewis Base Assisted Brønsted Base Catalysis: Direct Asymmetric Allylic Alkylation of Indenes

2011 ◽  
Vol 2011 (36) ◽  
pp. 7366-7371 ◽  
Author(s):  
Hai-Lei Cui ◽  
Xun-Hao Sun ◽  
Lin Jiang ◽  
Lin Dong ◽  
Ying-Chun Chen
Keyword(s):  
Lewis Base ◽  
Base Catalysis ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Brønsted Base

ChemInform Abstract: Lewis Base Assisted Broensted Base Catalysis: Direct Asymmetric Allylic Alkylation of Indenes.

ChemInform ◽  
2012 ◽  
Vol 43 (19) ◽  
pp. no-no
Author(s):  
Hai-Lei Chui ◽  
Xun-Hao Sun ◽  
Lin Jiang ◽  
Lin Dong ◽  
Yin-Chun Chen
Keyword(s):  
Lewis Base ◽  
Base Catalysis ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation

Lewis Base Assisted Brønsted Base Catalysis: Bidentate Phosphine Oxides as Activators and Modulators of Brønsted Basic Lanthanum-Aryloxides

2008 ◽  
Vol 47 (47) ◽  
pp. 9125-9129 ◽  
Author(s):  
Hiroyuki Morimoto ◽  
Tatsuhiko Yoshino ◽  
Takafumi Yukawa ◽  
Gang Lu ◽  
Shigeki Matsunaga ◽  
...  
Keyword(s):  
Lewis Base ◽  
Base Catalysis ◽  
Phosphine Oxides ◽  
Bidentate Phosphine ◽  
Brønsted Base

Copper/Lewis base cooperatively catalyzed asymmetric allylic alkylation of Morita−Baylis−Hillman carbonates with azomethine ylides

2021 ◽  
Author(s):  
Yimin Hu ◽  
Zhengyang Yan ◽  
Wangyu Shi ◽  
Jianning Liao ◽  
Min Liu ◽  
...  
Keyword(s):  
Lewis Base ◽  
Azomethine Ylides ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Cooperative Catalysis

In this paper, an asymmetric allylic alkylation of easily available azomethine ylides with Morita−Baylis−Hillman (MBH) Carbonates through a copper (I) / Lewis base cooperative catalysis strategy has been realized. The...

Unconventional Transformations of Morita–Baylis–Hillman Adducts

Synthesis ◽  
2020 ◽  
Author(s):  
Xavier Companyó ◽  
Alessio Calcatelli ◽  
Alessio Cherubini-Celli ◽  
Edoardo Carletti
Keyword(s):  
Transition Metal Complexes ◽  
Short Review ◽  
Lewis Base ◽  
Base Catalysis ◽  
Allylic Alkylation ◽  
One Pot ◽  
Allylic Alkylations ◽  
Cascade Processes ◽  
Dual Activation ◽  
Trisubstituted Alkenes

Morita–Baylis–Hillman (MBH) adducts are versatile starting materials widely employed in Lewis base catalysis. A myriad of different transformations have been reported based on either allylic alkylations with stabilised nucleophiles or annulations with diverse dipolarophiles. Apart from these two conventional types of reactivity, MBH adducts have recently been implemented in alternative and complementary catalytic strategies, including: (i) one-pot and cascade transformations, where additional chemical bonds are formed following the asymmetric allylic alkylation event in a single synthetic operation; (ii) regioselective α-allylations for the synthesis of trisubstituted alkenes; and (iii) dual activation strategies, involving Lewis base catalysis together with transition metal complexes or light, enabling allylic alkylations with nonstabilised nucleophiles and cascade processes. The present Short Review summarises the most significant unconventional catalytic transformations of racemic MBH adducts reported within the last decade.1 Introduction2 Multi-Step Single-Vessel Transformations (path iii)2.1 One-Pot Transformations2.2 Cascade Transformations3 α-Allylations (path iv)3.1 SN2′ Mechanism3.2 SN2′–SN2 Mechanism3.3 Miscellaneous Mechanisms4 Dual Activation (path v)4.1 MBH Adduct as Electrophile4.2 MBH Adduct as Nucleophile5 Summary and Outlook

Lewis Base Assisted Brønsted Base Catalysis: Bidentate Phosphine Oxides as Activators and Modulators of Brønsted Basic Lanthanum-Aryloxides

2008 ◽  
Vol 120 (47) ◽  
pp. 9265-9269 ◽  
Author(s):  
Hiroyuki Morimoto ◽  
Tatsuhiko Yoshino ◽  
Takafumi Yukawa ◽  
Gang Lu ◽  
Shigeki Matsunaga ◽  
...  
Keyword(s):  
Lewis Base ◽  
Base Catalysis ◽  
Phosphine Oxides ◽  
Bidentate Phosphine ◽  
Brønsted Base

Organocatalytic Group Transfer Reactions with Hypervalent Iodine­ Reagents

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 359-370 ◽  
Author(s):  
Marcin Kalek ◽  
Manoj Ghosh ◽  
Adam Rajkiewicz
Keyword(s):  
Short Review ◽  
Lewis Base ◽  
Base Catalysis ◽  
Synthetic Methods ◽  
Hypervalent Iodine ◽  
Group Transfer ◽  
Iodine Compounds ◽  
Amine Catalysis ◽  
Brønsted Base ◽  
Brønsted And Lewis Acid

In recent years, a plethora of synthetic methods that employ hypervalent iodine compounds donating an atom or a group of atoms to an acceptor molecule have been developed. Several of these transformations utilize organocatalysis, which complements well the economic and environmental advantages offered by iodine reagents. This short review provides a systematic survey of the organocatalytic approaches that have been used to promote group transfer from hypervalent iodine species. It covers both the reactions in which an organocatalyst is applied to activate the acceptor, as well as those that exploit the organocatalytic activation of the hypervalent iodine reagent itself.1 Introduction2 Organocatalytic Activation of Acceptor2.1 Amine Catalysis via Enamine and Unsaturated Iminium Formation2.2 NHC Catalysis via Acyl Anion Equivalent and Enolate Formation2.3 Chiral Cation Directed Catalysis and Brønsted Base Catalysis via Pairing with Stabilized Enolates3 Organocatalytic Activation of Hypervalent Iodine Reagent3.1 Brønsted and Lewis Acid Catalysis3.2 Lewis Base Catalysis3.3 Radical Reactions with Organic Promoters and Catalysts4 Summary and Outlook

Lewis Base Assisted Brønsted Base Catalysis: Direct Regioselective Asymmetric Vinylogous Alkylation of Allylic Sulfones

2011 ◽  
Vol 17 (34) ◽  
pp. 9489-9493 ◽  
Author(s):  
Lin Jiang ◽  
Qian Lei ◽  
Xin Huang ◽  
Hai-Lei Cui ◽  
Xue Zhou ◽  
...  
Keyword(s):  
Lewis Base ◽  
Base Catalysis ◽  
Brønsted Base

Organocatalytic enantioselective allylic alkylation of α-aryl γ-lactones: an approach to densely functionalized quaternary stereocentres

2020 ◽  
Vol 56 (49) ◽  
pp. 6640-6643
Author(s):  
Morgane Mando ◽  
Fabienne Grellepois ◽  
Emmanuel Riguet
Keyword(s):  
Lewis Base ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation

The asymmetric allylic alkylation of α-aryl γ-lactones involving the activation of Morita–Baylis–Hillman carbonates by an original chiral Lewis base is reported.

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