Phosphine-Catalyzed Asymmetric Allylic Alkylation of Achiral MBH Carbonates with 3,3′-Bisindolines: Enantioselective Construction of Quaternary Stereogenic Centers

2021 ◽  
Author(s):  
Chuan Xiang Alvin Tan ◽  
Guang-Jian Mei ◽  
Yixin Lu
Keyword(s):  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Stereogenic Centers ◽  
Quaternary Stereogenic Centers

Enantioselective Synthesis of Tertiary and Quaternary Stereogenic Centers: Copper/Phosphoramidite-Catalyzed Allylic Alkylation with Organolithium Reagents

2012 ◽  
Vol 124 (8) ◽  
pp. 1958-1961 ◽  
Author(s):  
Martín Fañanás-Mastral ◽  
Manuel Pérez ◽  
Pieter H. Bos ◽  
Alena Rudolph ◽  
Syuzanna R. Harutyunyan ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Allylic Alkylation ◽  
Stereogenic Centers ◽  
Organolithium Reagents ◽  
Quaternary Stereogenic Centers

Asymmetric Rhodium-Catalyzed Allylic Substitution Reactions with Nitrile-Stabilized Carbanions

Synlett ◽  
2021 ◽  
Author(s):  
Mai-Jan Tom ◽  
P. Andrew Evans
Keyword(s):  
Biologically Active ◽  
Allylic Alkylation ◽  
Substitution Reactions ◽  
Stereogenic Centers ◽  
Enantioselective Reactions ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Alkylation Reactions ◽  
Quaternary Stereogenic Centers ◽  
Selective Access

This Account summarizes our recent work on rhodium-catalyzed allylic alkylation reactions with nitrile-stabilized carbanions. Despite the challenges associated with employing nitrile stabilized nucleophiles in transition-metal-catalyzed reactions, we recently developed both enantiospecific and enantioselective allylic alkylation reactions. Notably, these novel reactions permit the expedient and selective access to an array of acyclic ternary and quaternary stereogenic centers that are present in important biologically active molecules. 1 Introduction 2 Enantiospecific Reactions of Nitrile-Stabilized Anions 3 Enantioselective Reactions of Nitrile-Stabilized Anions 4 Conclusion

Transition metal-free asymmetric and diastereoselective allylic alkylation using Grignard reagents: construction of vicinal stereogenic centers via kinetic resolution

2014 ◽  
Vol 5 (10) ◽  
pp. 3803-3807 ◽  
Author(s):  
David Grassi ◽  
Alexandre Alexakis
Keyword(s):  
Transition Metal ◽  
Kinetic Resolution ◽  
Grignard Reagents ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Quaternary Centers ◽  
Metal Free ◽  
Stereogenic Centers

The first transition metal-free catalyzed diastereoselective and enantioselective asymmetric allylic alkylation (AAA) has been disclosed leading to the construction of vicinal tertiary/quaternary centers via a kinetic resolution protocol starting from readily available starting materials.

scholarly journals Mechanistic insights into rhodium-catalyzed enantioselective allylic alkylation for quaternary stereogenic centers

2021 ◽  
Author(s):  
Monika Pareek ◽  
Raghavan B. Sunoj
Keyword(s):  
Allylic Alkylation ◽  
Stereogenic Centers ◽  
Quaternary Stereogenic Centers

The origin of high enantioselectivity in the formation of quaternary stereogenic carbon.

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