One-Step Stereocontrol of Three Contiguous Stereogenic Centers in Acyclic Systems: The Tuning Effect of an Additive in a Tandem Asymmetric Michael Addition and Meerwein–Ponndorf–Verley Reduction

2003 ◽  
Vol 42 (37) ◽  
pp. 4515-4517 ◽  
Author(s):  
Kiyoharu Nishide ◽  
Minoru Ozeki ◽  
Hideaki Kunishige ◽  
Yukihiro Shigeta ◽  
Pranab K. Patra ◽  
...  
Keyword(s):  
Michael Addition ◽  
Asymmetric Michael Addition ◽  
Stereogenic Centers ◽  
One Step

One-Step Stereocontrol of Three Contiguous Stereogenic Centers in Acyclic Systems: The Tuning Effect of an Additive in a Tandem Asymmetric Michael Addition and Meerwein–Ponndorf–Verley Reduction

2003 ◽  
Vol 115 (37) ◽  
pp. 4653-4655 ◽  
Author(s):  
Kiyoharu Nishide ◽  
Minoru Ozeki ◽  
Hideaki Kunishige ◽  
Yukihiro Shigeta ◽  
Pranab K. Patra ◽  
...  
Keyword(s):  
Michael Addition ◽  
Asymmetric Michael Addition ◽  
Stereogenic Centers ◽  
One Step

scholarly journals Synthesis of non-racemic 4-nitro-2-sulfonylbutan-1-ones via Ni(II)-catalyzed asymmetric Michael reaction of β-ketosulfones

2019 ◽  
Vol 15 ◽  
pp. 1289-1297 ◽  
Author(s):  
Alexander N Reznikov ◽  
Anastasiya E Sibiryakova ◽  
Marat R Baimuratov ◽  
Eugene V Golovin ◽  
Victor B Rybakov ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Bioactive Compounds ◽  
Michael Addition ◽  
Michael Reaction ◽  
High Yield ◽  
Michael Adducts ◽  
Significant Rate ◽  
Asymmetric Michael Addition ◽  
Stereogenic Centers ◽  
Asymmetric Michael Reaction

Functionally substituted sulfones with stereogenic centers are valuable reagents in organic synthesis and key motifs in some bioactive compounds. The asymmetric Michael addition of β-ketosulfones to conjugated nitroalkenes in the presence of Ni(II) complexes with various chiral vicinal diamines was studied. This reaction provides convenient access to non-racemic 4-nitro-2-sulfonylbutan-1-ones with two stereocenters with high yield and excellent enantioselectivity (up to 99%). It has been established that the catalytic Michael reaction itself was carried out with high diastereoselectivity, but the Michael adducts may epimerize at the C-2 position at a significant rate. Conditions for the preparation of individual diastereomers were found.

Cu(i)/TF-BiphamPhos-catalyzed asymmetric Michael addition of cyclic ketimino esters to alkylidene malonates

2015 ◽  
Vol 13 (19) ◽  
pp. 5460-5466 ◽  
Author(s):  
Zhi-Yong Xue ◽  
Zhi-Min Song ◽  
Chun-Jiang Wang
Keyword(s):  
Amino Acids ◽  
Michael Addition ◽  
Asymmetric Michael Addition ◽  
Stereogenic Centers ◽  
Efficient Construction

Cu(i)-catalyzed asymmetric Michael addition of cyclic ketimino esters with alkylidene malonates has been developed for efficient construction of β-branched α-amino acids containing adjacent quaternary and tertiary stereogenic centers in good yields with excellent diastereo-/enantioselectivities.

Pyrrolidinyl-Camphor Derivatives as a New Class of Organocatalyst for Direct Asymmetric Michael Addition of Aldehydes and Ketones to β-Nitroalkenes

2010 ◽  
Vol 16 (23) ◽  
pp. 7030-7038 ◽  
Author(s):  
Ying-Fang Ting ◽  
Chihliang Chang ◽  
Raju Jannapu Reddy ◽  
Dhananjay R. Magar ◽  
Kwunmin Chen
Keyword(s):  
Michael Addition ◽  
New Class ◽  
Asymmetric Michael Addition ◽  
Aldehydes And Ketones ◽  
Camphor Derivatives

ChemInform Abstract: Asymmetric Michael Addition of Ketones to Nitroolefins: Pyrrolidinyl-oxazole-carboxamides as New Efficient Organocatalysts.

ChemInform ◽  
2015 ◽  
Vol 46 (12) ◽  
pp. no-no
Author(s):  
Ahmed Kamal ◽  
Manda Sathish ◽  
Vunnam Srinivasulu ◽  
Jadala Chetna ◽  
Kunta Chandra Shekar ◽  
...  
Keyword(s):  
Michael Addition ◽  
Asymmetric Michael Addition

scholarly journals Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

2017 ◽  
Vol 13 ◽  
pp. 612-619 ◽  
Author(s):  
Alejandro Castán ◽  
Ramón Badorrey ◽  
José A Gálvez ◽  
María D Díaz-de-Villegas
Keyword(s):  
Michael Addition ◽  
Bulky Substituent ◽  
Asymmetric Michael Addition ◽  
Iodination Reaction ◽  
Chiral Imines ◽  
New Compounds ◽  
The Michael Addition

New pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (R)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved.

Sign in / Sign up

Export Citation Format

Share Document