Organocatalytic asymmetric synthesis of benzothiazolopyrimidines via [4+2] cycloaddition of azlactones with 2-benzothiazolimines

2021 ◽  
Author(s):  
Chaoqi Ke ◽  
Zhenzhong Liu ◽  
Sai Ruan ◽  
Xiaoming Feng ◽  
Xiaohua Liu
Keyword(s):  
Asymmetric Synthesis ◽  
Stereogenic Centers ◽  
Quaternary Stereogenic Centers

An easily available L-proline-derived guanidine-amide was found efficient to catalyze [4+2] cycloaddition of azlactones with 2-benzothiazolimines, affording various benzothiazolopyrimidines bearing adjacent tertiary and quaternary stereogenic centers in excellent results at...

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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