scholarly journals Synthesis of Adjacent Quaternary Stereocenters by Catalytic Asymmetric Allylboration

2015 ◽  
Vol 137 (35) ◽  
pp. 11262-11265 ◽  
Author(s):  
Rauful Alam ◽  
Tobias Vollgraff ◽  
Lars Eriksson ◽  
Kálmán J. Szabó
Keyword(s):  
Catalytic Asymmetric ◽  
Quaternary Stereocenters

scholarly journals Highly Enantioselective Construction of Quaternary Stereocenters onβ-Keto Esters by Phase-Transfer Catalytic Asymmetric Alkylation and Michael Reaction

2003 ◽  
Vol 115 (34) ◽  
pp. 4111-4111 ◽  
Author(s):  
Takashi Ooi ◽  
Takashi Miki ◽  
Mika Taniguchi ◽  
Misato Shiraishi ◽  
Mifune Takeuchi ◽  
...  
Keyword(s):  
Michael Reaction ◽  
Phase Transfer ◽  
Asymmetric Alkylation ◽  
Keto Esters ◽  
Catalytic Asymmetric ◽  
Quaternary Stereocenters

Catalytic asymmetric synthesis of pyrrolidine derivatives bearing heteroatom-substituted quaternary stereocenters

2018 ◽  
Vol 5 (1) ◽  
pp. 36-40 ◽  
Author(s):  
Zhi-Peng Wang ◽  
Qi Wu ◽  
Jia Jiang ◽  
Zi-Rui Li ◽  
Xiao-Jiao Peng ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric ◽  
Quaternary Stereocenters

An enantioselective [3 + 2] cycloaddition of heteroatom-substituted alkenes with α-substituted isocyanoacetates has been developed. Excellent reactivity and enantioselectivity were obtained.

scholarly journals Pentanidium-Catalyzed Direct Assembly of Vicinal All-Carbon Quaternary Stereocenters through C(sp3)-C(sp3) Bond Formation

2021 ◽  
Author(s):  
Choon-Hong Tan ◽  
Xu Ban ◽  
Yifan Fan ◽  
Tuan-Khoa Kha ◽  
Richmond Lee ◽  
...  
Keyword(s):  
Bond Formation ◽  
Direct Assembly ◽  
Tertiary Carbon ◽  
Asymmetric Coupling ◽  
Catalytic Asymmetric ◽  
Quaternary Stereocenters ◽  
Straightforward Approach

Abstract The stereoselective construction of vicinal all-carbon quaternary stereocenters has long been a formidable synthetic challenge. Direct asymmetric coupling of a tertiary carbon nucleophile with a tertiary carbon electrophile is the most straightforward approach but it is sterically and energetically disfavored. Herein, we described a catalytic asymmetric substitution, where racemic tertiary bromides directly couple with racemic secondary or tertiary carbanion, creating a series of congested carbon (sp3)-carbon(sp3) bonds, including isolated all-carbon quaternary stereocenters, vicinal tertiary/all-carbon quaternary stereocenters and vicinal all-carbon quaternary stereocenters. This double stereoconvergent process, using pentanidium as catalyst, affords substituted products in good enantioselectivities and diastereoselectivities.

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