Organocatalytic Michael Addition of Naphthoquinone with α,β-Unsaturated Ketones: Primary Amine Catalyzed Asymmetric Synthesis of Lapachol Analogues

2011 ◽  
Vol 2011 (11) ◽  
pp. 2142-2147 ◽  
Author(s):  
Guangcun Zhang ◽  
Yifeng Wang ◽  
Wei Zhang ◽  
Xiangsheng Xu ◽  
Aiguo Zhong ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Primary Amine ◽  
Unsaturated Ketones

ChemInform Abstract: Organocatalytic Michael Addition of Naphthoquinone with α,β-Unsaturated Ketones: Primary Amine Catalyzed Asymmetric Synthesis of Lapachol Analogues.

ChemInform ◽  
2011 ◽  
Vol 42 (30) ◽  
pp. no-no
Author(s):  
Guangcun Zhang ◽  
Yifeng Wang ◽  
Wei Zhang ◽  
Xiangsheng Xu ◽  
Aiguo Zhong ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Primary Amine ◽  
Unsaturated Ketones

Enantioselective cascade double Michael addition of 3-nitro-2H-chromenes and acyclic enones: efficient synthesis of functionalized tricyclic chroman derivatives

2015 ◽  
Vol 13 (37) ◽  
pp. 9600-9609 ◽  
Author(s):  
Jun-Hua Li ◽  
Da-Ming Du
Keyword(s):  
Michael Addition ◽  
Primary Amine ◽  
Efficient Synthesis ◽  
Unsaturated Ketones

An efficient protocol for the construction of enantiomerically enriched tetrahydro-6H-benzo[c]chromenes by the cascade double Michael addition of 3-nitro-2H-chromenes and α,β-unsaturated ketones catalyzed by a quinine-derived primary amine has been developed.

Asymmetric Sulfa-Michael Addition to α-Substituted Vinyl Ketones Catalyzed by Chiral Primary Amine

2014 ◽  
Vol 16 (17) ◽  
pp. 4626-4629 ◽  
Author(s):  
Niankai Fu ◽  
Long Zhang ◽  
Sanzhong Luo ◽  
Jin-Pei Cheng
Keyword(s):  
Michael Addition ◽  
Primary Amine

Highly enantioselective aza-Michael addition reactions of 4-nitrophthalimide with α,β-unsaturated ketones

RSC Advances ◽  
2013 ◽  
Vol 3 (29) ◽  
pp. 11498 ◽  
Author(s):  
Shijun Ma ◽  
Lulu Wu ◽  
Ming Liu ◽  
Xiufang Xu ◽  
Yaodong Huang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Addition Reactions ◽  
Unsaturated Ketones

Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction

Science ◽  
2018 ◽  
Vol 360 (6396) ◽  
pp. 1438-1442 ◽  
Author(s):  
Jianfeng Chen ◽  
Xing Gong ◽  
Jianyu Li ◽  
Yingkun Li ◽  
Jiguo Ma ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
High Activity ◽  
Asymmetric Catalysis ◽  
Carbonyl Group ◽  
Mannich Reaction ◽  
Primary Amine ◽  
Chiral Amines ◽  
Carbonyl Groups ◽  
Diphenylphosphinyl Imines

Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N-diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis.

Asymmetric Synthesis of an Amino Acid Derivative from Achiral Aroyl Acrylamide by Reversible Michael Addition and Preferential Crystallization

2016 ◽  
Vol 22 (46) ◽  
pp. 16429-16432 ◽  
Author(s):  
Yuki Kaji ◽  
Naohiro Uemura ◽  
Yoshio Kasashima ◽  
Hiroki Ishikawa ◽  
Yasushi Yoshida ◽  
...  
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Acid Derivative ◽  
Michael Addition ◽  
Amino Acid Derivative
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