Assembly of Fluorinated Quaternary Stereogenic Centers through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions

2015 ◽  
Vol 127 (20) ◽  
pp. 6117-6121 ◽  
Author(s):  
Chen Xie ◽  
Lingmin Wu ◽  
Jianlin Han ◽  
Vadim A. Soloshonok ◽  
Yi Pan
Keyword(s):  
Aldol Reactions ◽  
Stereogenic Centers ◽  
Quaternary Stereogenic Centers

Catalytic asymmetric aldol addition reactions of 3-fluoro-indolinone derived enolates

2017 ◽  
Vol 15 (2) ◽  
pp. 311-315 ◽  
Author(s):  
Lijun Zhang ◽  
Wenzhong Zhang ◽  
Haibo Mei ◽  
Jianlin Han ◽  
Vadim A. Soloshonok ◽  
...  
Keyword(s):  
Aldol Reactions ◽  
Addition Reactions ◽  
Asymmetric Aldol ◽  
Wide Range ◽  
Stereogenic Centers ◽  
New Type ◽  
Catalytic Asymmetric ◽  
Aldol Addition ◽  
Quaternary Stereogenic Centers

Cu(i)/bisoxazoline ligand catalyzed asymmetric aldol reactions of fluoro-indolinone derived new type tertiary enolates have been developed. This process allows the preparation of a wide range of α-fluoro-β-aryl/hetaryl/alkyl-β-hydroxy-indolin-2-one products containing C–F quaternary stereogenic centers.

All-Carbon Quaternary Stereogenic Centers in Acyclic Systems through the Creation of Several C–C Bonds per Chemical Step

2014 ◽  
Vol 136 (7) ◽  
pp. 2682-2694 ◽  
Author(s):  
Ilan Marek ◽  
Yury Minko ◽  
Morgane Pasco ◽  
Tom Mejuch ◽  
Noga Gilboa ◽  
...  
Keyword(s):  
Stereogenic Centers ◽  
The Creation ◽  
Quaternary Stereogenic Centers

Chirality Transfer from a Chiral Primary Alcohol Equivalent Through Allyl Cyanate-to-Isocyanate Rearrangement: Synthesis of (+)-Geranyllinaloisocyanide

Synthesis ◽  
2019 ◽  
Vol 51 (15) ◽  
pp. 2959-2964 ◽  
Author(s):  
Yoshiyasu Ichikawa ◽  
Hirofumi Morimoto ◽  
Toshiya Masuda
Keyword(s):  
Natural Product ◽  
Primary Alcohol ◽  
Marine Natural Product ◽  
Chirality Transfer ◽  
New Approach ◽  
Stereogenic Centers ◽  
Quaternary Stereogenic Centers

A new approach was developed to construct quaternary stereogenic centers bearing nitrogen substituents in an enantioselective manner. The strategy takes advantage of [1,3]-chirality transfer from a chiral primary alcohol equivalent through an allyl cyanate-to-isocyanate rearrangement. This approach was employed in an efficient eight-step synthesis of the marine natural product, (+)-geranyllinaloisocyanide, in 43% overall yield.

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