A Highly Diastereoselective Decarboxylative Mannich Reaction of β-Keto Acids with Optically Active N-Sulfinyl α-Imino Esters

2012 ◽  
Vol 14 (12) ◽  
pp. 3092-3095 ◽  
Author(s):  
Cui-Feng Yang ◽  
Chen Shen ◽  
Jian-Yong Wang ◽  
Shi-Kai Tian
Keyword(s):  
Mannich Reaction ◽  
Optically Active ◽  
Keto Acids ◽  
Imino Esters

Bifunctional squaramide catalyzed stereoselective Mannich reaction of α-azido ketones with isatin-derived ketimines

2020 ◽  
Vol 18 (3) ◽  
pp. 479-487 ◽  
Author(s):  
Seda Karahan ◽  
Cihangir Tanyeli
Keyword(s):  
Mannich Reaction ◽  
Optically Active ◽  
First Time ◽  
High Stereoselectivity

Bifunctional squaramide catalyzed asymmetric Mannich reaction of alpha-azido ketones and isatin derived ketiminines were established for the first time with high stereoselectivity. Adducts are valuable synthons for optically active heterocycles.

Integrated reactions based on the sequential addition to α-imino esters

2014 ◽  
Vol 86 (5) ◽  
pp. 755-764 ◽  
Author(s):  
Kaichiro Koyama ◽  
Isao Mizota ◽  
Makoto Shimizu
Keyword(s):  
Mannich Reaction ◽  
Addition Reaction ◽  
Imino Nitrogen ◽  
Crucial Step ◽  
Sequential Addition ◽  
Imino Esters ◽  
Sequential Reactions

AbstractThis article summarizes integrated sequential reactions with α-imino esters, where the umpolung addition reaction to the imino nitrogen followed by the second addition or oxidation is the crucial step. The following four types of reactions are discussed: (1) tandem N-ethylation/Mannich reaction; (2) N-alkylation/addition reaction; (3) synthesis of indolin-3-ones and tetrahydro-4-quinolones; (4) regioselective tandem N-alkylation/ C-acylation of β,γ-alkynyl α-imino esters.

Catalytic asymmetric addition reactions leading to carbon-carbon bond formation: Phenyl and alkenyl transfer to aldehydes and alkynylation of α-imino esters

2006 ◽  
Vol 78 (2) ◽  
pp. 267-274 ◽  
Author(s):  
Jian-Xin Ji ◽  
Jing Wu ◽  
Lijin Xu ◽  
Chiu-Wing Yip ◽  
Kim Hung Lam ◽  
...  
Keyword(s):  
Bond Formation ◽  
Optically Active ◽  
Amino Acid Derivatives ◽  
Addition Reactions ◽  
Terminal Alkynes ◽  
Reaction Conditions ◽  
Carbon Carbon Bond ◽  
Catalytic Asymmetric ◽  
High Yields ◽  
Imino Esters

Optically active tertiary aminonaphthol ligands were obtained by a new, convenient procedure and were found to catalyze the enantioselective alkenyl and phenyl transfer to aldehydes in high yields and excellent enantiomeric excesses (ee's). The catalytic asymmetric introduction of alkynyl functionality to α-amino acid derivatives was realized by the direct addition of terminal alkynes to α-imino ester in the presence of chiral copper(I) complex under mild reaction conditions.

Catalytic Approach for the Formation of Optically Active Allyl α-Amino Acids by Addition of Allylic Metal Compounds to α-Imino Esters

1999 ◽  
Vol 64 (13) ◽  
pp. 4844-4849 ◽  
Author(s):  
Xiangming Fang ◽  
Mogens Johannsen ◽  
Sulan Yao ◽  
Nicholas Gathergood ◽  
Rita G. Hazell ◽  
...  
Keyword(s):  
Amino Acids ◽  
Optically Active ◽  
Metal Compounds ◽  
Imino Esters

scholarly journals Asymmetric organocatalytic decarboxylative Mannich reaction using β-keto acids: A new protocol for the synthesis of chiral β-amino ketones

2012 ◽  
Vol 8 ◽  
pp. 1279-1283 ◽  
Author(s):  
Chunhui Jiang ◽  
Fangrui Zhong ◽  
Yixin Lu
Keyword(s):  
Mannich Reaction ◽  
Keto Acids

The first decarboxylative Mannich reaction employing β-keto acids, catalyzed by cinchonine-derived bifunctional thiourea catalyst has been described. The desired β-amino ketones were obtained in excellent yields and with moderate to good enantioselectivities.

The use of two optically active N-sulfinyl α-imino esters in the stereoselective aza-Diels–Alder reaction

Tetrahedron ◽  
2009 ◽  
Vol 65 (14) ◽  
pp. 2806-2817 ◽  
Author(s):  
Trygve Andreassen ◽  
Marianne Lorentzen ◽  
Lars-Kristian Hansen ◽  
Odd R. Gautun
Keyword(s):  
Alder Reaction ◽  
Optically Active ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Imino Esters
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