Regio- and Stereoselectivity in the Reactions of Organometallic Reagents with an Electron-Deficient and an Electron-Rich Vinyloxirane: Applications for Sequential Bis-Allylic Substitution Reactions in the Generation of Vicinal Stereogenic Centers

2012 ◽  
Vol 77 (11) ◽  
pp. 4949-4967 ◽  
Author(s):  
R. Karl Dieter ◽  
Yaxin Huang ◽  
Fenghai Guo
Keyword(s):  
Allylic Substitution ◽  
Substitution Reactions ◽  
Organometallic Reagents ◽  
Stereogenic Centers

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: Asymmetric Allylic Substitution Reactions with a Xylophos-Pd Catalyst.

ChemInform ◽  
2001 ◽  
Vol 32 (9) ◽  
pp. no-no
Author(s):  
Oscar Pamies ◽  
Aurora Ruiz ◽  
Gemma Net ◽  
Carmen Claver ◽  
Hermann Kalchhauser ◽  
...  
Keyword(s):  
Pd Catalyst ◽  
Allylic Substitution ◽  
Substitution Reactions

scholarly journals Progress in Iridium-Catalyzed Asymmetric Allylic Substitution Reactions via Synergetic Catalysis

2020 ◽  
Vol 40 (10) ◽  
pp. 3262
Author(s):  
Fei Tian ◽  
Jian Zhang ◽  
Wulin Yang ◽  
Weiping Deng
Keyword(s):  
Allylic Substitution ◽  
Substitution Reactions
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