Hindered Brønsted bases as Lewis base catalysts

2009 ◽  
Vol 7 (19) ◽  
pp. 4009 ◽  
Author(s):  
Sobia Tabassum ◽  
Oksana Sereda ◽  
Peddiahgari Vasu Govardhana Reddy ◽  
René Wilhelm
Keyword(s):  
Lewis Base ◽  
Base Catalysts ◽  
Lewis Base Catalysts

scholarly journals Developing a Methodology for Catalytic Asymmetric Crotylation of Aldehydes

Synlett ◽  
2021 ◽  
Author(s):  
Andrei V. Malkov ◽  
Aleksandr E. Rubtsov
Keyword(s):  
Kinetic Resolution ◽  
Lewis Base ◽  
Chiral Auxiliaries ◽  
Organometallic Reagents ◽  
Total Syntheses ◽  
Base Catalysts ◽  
Homoallylic Alcohols ◽  
Stereogenic Centers ◽  
Long Time ◽  
Lewis Base Catalysts

AbstractAsymmetric crotylation has firmly earned a place among the set of valuable synthetic tools for stereoselective construction of carbon skeletons. For a long time the field was heavily dominated by reagents bearing stoichiometric chiral auxiliaries, but now catalytic methods are gradually taking center stage, and the area continues to develop rapidly. This account focuses primarily on preformed organometallic reagents based on silicon and, to some extent, boron. It narrates our endeavors to design new and efficient chiral Lewis base catalysts for the asymmetric addition of crotyl(trichloro)silanes to aldehydes. It also covers the development of a novel protocol for kinetic resolution of racemic secondary allylboronates to give enantio- and diastereomerically enriched linear homoallylic alcohols. As a separate topic, cross-crotylation of aldehydes by using enantiopure branched homoallylic alcohols as a source of crotyl groups is discussed. Finally, the synthetic credentials of the developed methodology are illustrated by total syntheses of marine natural products, in which crotylation plays a key role in setting up stereogenic centers.1 Introduction2 Pyridine N-Oxides as Lewis Base Catalysts3 Bipyridine N,N′-Dioxides as Lewis Base Catalysts4 Chiral Allylating Reagents5 Synthetic Applications6 Concluding Remarks

ChemInform Abstract: Chiral Cobalt(III) Complexes as Bifunctional Broensted Acid-Lewis Base Catalysts for the Preparation of Cyclic Organic Carbonates.

ChemInform ◽  
2016 ◽  
Vol 47 (22) ◽  
Author(s):  
Yuri A. Rulev ◽  
Vladimir A. Larionov ◽  
Anastasia V. Lokutova ◽  
Margarita A. Moskalenko ◽  
Ol'ga L. Lependina ◽  
...  
Keyword(s):  
Lewis Base ◽  
Base Catalysts ◽  
Organic Carbonates ◽  
Lewis Base Catalysts

scholarly journals Biocatalytic Dynamic Kinetic Resolution for the Synthesis of Atropisomeric Biaryl N-Oxide Lewis Base Catalysts

2016 ◽  
Vol 128 (36) ◽  
pp. 10913-10917 ◽  
Author(s):  
Samantha Staniland ◽  
Ralph W. Adams ◽  
Joseph J. W. McDouall ◽  
Irene Maffucci ◽  
Alessandro Contini ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Lewis Base ◽  
Dynamic Kinetic Resolution ◽  
Base Catalysts ◽  
Lewis Base Catalysts

scholarly journals Polarity Inversion Catalysis by the 1,4-Addition of N-Heterocyclic Carbenes

2020 ◽  
Vol 73 (1) ◽  
pp. 1 ◽  
Author(s):  
Xuan B. Nguyen ◽  
Yuji Nakano ◽  
David W. Lupton
Keyword(s):  
Catalytic Reaction ◽  
Heterocyclic Carbenes ◽  
Lewis Base ◽  
Coupling Reactions ◽  
Polarity Inversion ◽  
Contrast Polarity ◽  
Base Catalysts ◽  
Selection For ◽  
Lewis Base Catalysts ◽  
Comprehensive Coverage

Polarity inversion is the hallmark of N-heterocyclic carbene (NHC) organocatalysis, with the generation and reaction of acyl anion equivalents known for more than 70 years. In contrast, polarity inversion through 1,4-addition of NHCs to conjugate acceptors was first applied in a catalytic reaction in 2006. This sub-field of NHC-organocatalysis has developed steadily over the subsequent years, enabling novel coupling reactions, enantioselective cycloisomerizations, polymerizations, and other reactions. In this review, this emerging area of NHC-organocatalysis is discussed with comprehensive coverage. In addition, notes regarding the use of other Lewis base catalysts for related reactions, and comments regarding NHC selection for this type of catalysis, are provided.

Two polyoxoniobates-based ionic crystals as Lewis base catalysts for cyanosilylation

2020 ◽  
Vol 111 ◽  
pp. 107666 ◽  
Author(s):  
Shujun Li ◽  
Panpan Ji ◽  
Shangning Han ◽  
Zhaomin Hao ◽  
Xuenian Chen
Keyword(s):  
Lewis Base ◽  
Ionic Crystals ◽  
Base Catalysts ◽  
Lewis Base Catalysts

ChemInform Abstract: Ureas: New Efficient Lewis Base Catalysts for the Allylation of Aldehydes.

ChemInform ◽  
2010 ◽  
Vol 30 (30) ◽  
pp. no-no
Author(s):  
Isabelle Chataigner ◽  
Umberto Piarulli ◽  
Cesare Gennari
Keyword(s):  
Lewis Base ◽  
Base Catalysts ◽  
Lewis Base Catalysts

scholarly journals Polymer-Supported Chiral Lewis Base Catalysts

Synfacts ◽  
2005 ◽  
Vol 2005 (00) ◽  
pp. 0089-0089
Keyword(s):  
Lewis Base ◽  
Base Catalysts ◽  
Polymer Supported ◽  
Lewis Base Catalysts

Latent (Pro)Nucleophiles in Enantioselective Lewis Base Catalyzed Allylic Substitutions

Synlett ◽  
2020 ◽  
Vol 31 (13) ◽  
pp. 1237-1243
Author(s):  
Ivan Vilotijevic ◽  
Markus Lange ◽  
You Zi
Keyword(s):  
Driving Force ◽  
Lewis Base ◽  
Base Catalysts ◽  
Allylic Substitutions ◽  
Opportune Time ◽  
Catalyzed Reactions ◽  
Lewis Base Catalysts

The use of latent nucleophiles, which are molecules that are not nucleophilic but can be activated to act as a nucleophile at an opportune time during the reaction, expands the scope of Lewis base catalyzed reactions. Here, we provide an overview of the concept and show examples of applications to N- and C-centered nucleophiles in allylic substitutions. N- and C-silyl compounds are superior latent (pro)nucleophiles in Lewis base catalyzed reactions with allylic fluorides in which the formation of the strong Si–F bond serves as the driving force for the reactions. The latent (pro)nucleophiles ensure high regio­selectivity in these reactions and enable enantioselective transformations of Morita–Baylis–Hillman adducts by the use of common chiral Lewis base catalysts.1 Introduction2 Substitution of MBH Carbonates3 The Concept of Latent (Pro)Nucleophiles4 Enantioselective Allylation of N-Heterocycles5 Enantioselective Phosphonyldifluoromethylation of Allylic Fluorides6 Conclusion

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