Novel and practical asymmetric synthesis of β 2,3 -amino esters using asymmetric Michael addition of chiral amine

Tetrahedron ◽  
2017 ◽  
Vol 73 (15) ◽  
pp. 2014-2021
Author(s):  
Minoru Ozeki ◽  
Honoka Egawa ◽  
Toshiki Takano ◽  
Hideki Mizutani ◽  
Narumi Yasuda ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Chiral Amine ◽  
Amino Esters ◽  
Asymmetric Michael Addition

scholarly journals Efficient Asymmetric Synthesis of Prostaglandin E1

2007 ◽  
Vol 62 (4) ◽  
pp. 556-560 ◽  
Author(s):  
Jae-Chul Jung ◽  
Oee-Sook Park
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Prostaglandin E1 ◽  
Simple Synthesis ◽  
High Yield ◽  
Prostaglandin E ◽  
Magnesium Bromide ◽  
One Pot ◽  
Asymmetric Michael Addition ◽  
Key Steps

A simple synthesis of prostaglandin E1 (PGE1) is described. The key steps are an asymmetric Michael addition to establish the desired (R)-configurations at C8 and C12 of the 2- (trimethylsilyl)ethoxymethyl- (SEM) protected PGE1 and its one-pot deprotection with magnesium bromide in high yield. This method is potentially useful for the preparation of other modified prostaglandins.

scholarly journals Asymmetric Michael addition using sugar derived organocatalysts

2017 ◽  
Vol 17 (4) ◽  
pp. 182-196
Author(s):  
P.B. Lalthanpuii ◽  
C. Lalhriatpuia ◽  
K. Vanlaldinpuia
Keyword(s):  
Molecular Weight ◽  
Asymmetric Synthesis ◽  
Present Article ◽  
Asymmetric Catalysis ◽  
Michael Addition ◽  
Metal Contamination ◽  
Low Molecular Weight ◽  
Asymmetric Transformations ◽  
Asymmetric Michael Addition ◽  
Different Types

Sugars are low-molecular-weight carbohydrates which consist of polyhydroxyl and carbonyl (aldehyde or ketone) functional groups. Different types of compounds derived from sugars have been used extensively as powerful and effective catalysts for asymmetric synthesis. They are readily available at a reasonable price, easily prepared, no metal contamination and are inert towards moisture and air. They are highly functionalized and have well defined stereogenic centres. Most of them are employed as chiral ligands in metal based asymmetric catalysis and are used for various asymmetric transformations. Different compounds derived from sugars have also been used recently as organocatalysts for asymmetric synthesis. The present article provides some of the organocatalysts used for asymmetric synthesis.

Asymmetric Synthesis of Adamantyl GABA Analogues

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 463-469 ◽  
Author(s):  
Anastasiya Sibiryakova ◽  
Vadim Shiryaev ◽  
Alexander Reznikov ◽  
Anastasiya Kabanova ◽  
Yuri Klimochkin
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Diethyl Malonate ◽  
Efficient Synthesis ◽  
Synthetic Strategy ◽  
Asymmetric Michael Addition ◽  
Gaba Analogues ◽  
Sterically Hindered

An efficient synthesis of (R)- and (S)-4-amino-3-(adamant-1-yl)butyric acids and (R)- and (S)-4-(adamant-1-yl)pyrrolidin-2-ones is presented. The synthetic strategy is based on asymmetric Michael addition of diethyl malonate to 1-(adamant-1-yl)-2-nitroethene using available Ni(II) complex as the catalyst. The procedures provide good to high enantioselectivity of Michael addition to sterically hindered nitroalkene and good yields of (R)- and (S)-enantiomers of 3-adamantyl substituted GABA.

Direct asymmetric Michael addition of thioether-based aryl sulfanyl-propan-2-one to nitroalkenes catalyzed by a chiral amine-thiourea bifunctional organocatalyst

Chirality ◽  
2010 ◽  
Vol 22 (7) ◽  
pp. 625-634 ◽  
Author(s):  
Xianxing Jiang ◽  
Bangzhi Zhang ◽  
Yifu Zhang ◽  
Li Lin ◽  
Wenjin Yan ◽  
...  
Keyword(s):  
Michael Addition ◽  
Chiral Amine ◽  
Asymmetric Michael Addition

Asymmetric Michael Addition of a Recyclable Chiral Amine: Inversion of Stereoselectivity Caused by the Difference of Ethereal Solvents

2008 ◽  
Vol 10 (13) ◽  
pp. 2653-2656 ◽  
Author(s):  
Manabu Node ◽  
Daisuke Hashimoto ◽  
Takahiro Katoh ◽  
Shunsuke Ochi ◽  
Minoru Ozeki ◽  
...  
Keyword(s):  
Michael Addition ◽  
Chiral Amine ◽  
Asymmetric Michael Addition ◽  
The Difference

Chiral Amine-Thiourea Catalyst for the Asymmetric Michael Addition

Synfacts ◽  
2006 ◽  
Vol 2006 (7) ◽  
pp. 0727-0727
Author(s):  
E. Jacobsen ◽  
H. Huang
Keyword(s):  
Michael Addition ◽  
Chiral Amine ◽  
Asymmetric Michael Addition

ChemInform Abstract: Asymmetric Synthesis of 4-Substituted 2,6-Dioxopiperidine-3-carbonitrile by Using Thiourea-Catalyzed Asymmetric Michael Addition.

ChemInform ◽  
2009 ◽  
Vol 40 (40) ◽  
Author(s):  
Tsubasa Inokuma ◽  
Yuuki Nagamoto ◽  
Shota Sakamoto ◽  
Hideto Miyabe ◽  
Kiyosei Takasu ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Asymmetric Michael Addition

Rawal's catalyst as an effective stimulant for the highly asymmetric Michael addition of β-keto esters to functionally rich nitro-olefins

2016 ◽  
Vol 14 (24) ◽  
pp. 5494-5499 ◽  
Author(s):  
A. Suresh Kumar ◽  
T. Prabhakar Reddy ◽  
R. Madhavachary ◽  
Dhevalapally B. Ramachary
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Amino Group ◽  
Keto Esters ◽  
Asymmetric Michael Addition ◽  
Dehydration Reactions

A general approach to the asymmetric synthesis of highly substituted dihydroquinolines was achieved through neighboring ortho-amino group engaged sequential Michael/amination/dehydration reactions.

scholarly journals Asymmetric Synthesis of (+)-Hinokinin, (+)-Dihydrocubebin and Cubebin Dimethyl Ether, a New Lignan from Phyllanthus niruri

2007 ◽  
Vol 62 (1) ◽  
pp. 117-120 ◽  
Author(s):  
Dieter Enders ◽  
Mile Milovanović
Keyword(s):  
Asymmetric Synthesis ◽  
Dimethyl Ether ◽  
Michael Addition ◽  
Phyllanthus Niruri ◽  
Asymmetric Michael Addition

The asymmetric synthesis of the new lignan cubebin dimethyl ether was accomplished in eight steps with an overall yield of 40 %. In addition, the known lignans (+)-hinokinin and (+)-dihydrocubebin were synthesized by this route. Our approach involves the highly diastereoselective and enantioselective (de ≥ 98%, ee ≥ 98%) construction of a trans-substituted 2,3- dibenzylbutyrolactone through an asymmetric Michael addition of an enantiopure lithiated aminonitrile to 5H-furan-2-one.

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