Ruthenium-Catalyzed Intermolecular Coupling of Vinylic 1,2-Bisboronates with Alkynes: Stereoselective Access to Boryl-Substituted Homoallylic Alcohols

2020 ◽  
Vol 142 (16) ◽  
pp. 7312-7316 ◽  
Author(s):  
Barry M. Trost ◽  
Guoting Zhang
Keyword(s):  
Homoallylic Alcohols ◽  
Intermolecular Coupling

Synthesis of Functionalized Homoallylic Alcohols Using Potassium Allyltrifluoroborate Promoted by Microwave Irradiation

2015 ◽  
Vol 2 (4) ◽  
pp. 403-408 ◽  
Author(s):  
Gilson B. da Silva ◽  
Jucleiton J. R. de Freitas ◽  
Paulo H. Menezes ◽  
Ivani Malvestiti
Keyword(s):  
Microwave Irradiation ◽  
Homoallylic Alcohols

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

Synthesis of Enantiopure Homoallylic Alcohols

1998 ◽  
Vol 4 (9) ◽  
pp. 1862-1869 ◽  
Author(s):  
Lutz F. Tietze ◽  
Kai Schiemann ◽  
Christoph Wegner ◽  
Christian Wulff
Keyword(s):  
Homoallylic Alcohols

Titanium-Mediated [2 + 2 + 2] Coupling of Diynes with Homoallylic Alcohols.

ChemInform ◽  
2003 ◽  
Vol 34 (40) ◽  
Author(s):  
Moo Je Sung ◽  
Jin-Hyun Pang ◽  
Soon-Bong Park ◽  
Jin Kun Cha
Keyword(s):  
Homoallylic Alcohols
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