Stereodivergent Silver-Catalyzed Synthesis of Pyroglutamic Acid Esters

2021 ◽  
Author(s):  
Byungjun Kim ◽  
Yuna Song ◽  
Sarah Yunmi Lee
Keyword(s):  
Conjugate Addition ◽  
Pyroglutamic Acid ◽  
Acid Esters

We report here a silver-catalyzed method for the enantio- and diastereodivergent synthesis of chiral pyroglutamic acid esters with multiple stereocenters. This process proceeds through asymmetric conjugate addition of glycine imine...

Enantioselective Synthesis of Pyroglutamic Acid Esters from Glycinate via Carbonyl Catalysis

2021 ◽  
Author(s):  
Baoguo Zhao ◽  
Jiguo Ma ◽  
Qinghai Zhou ◽  
Guanshui Song ◽  
Yongchang Song ◽  
...  
Keyword(s):  
Pyroglutamic Acid ◽  
Enantioselective Synthesis ◽  
Acid Esters

Efficient Synthesis of (R)- and (S)-α-(Hydroxymethyl)pyroglutamic Acid Esters from l-Proline

Synthesis ◽  
2009 ◽  
Vol 2009 (22) ◽  
pp. 3751-3756 ◽  
Author(s):  
Tetsuro Shinada ◽  
Yasufumi Ohfune ◽  
Hiroki Yoshida
Keyword(s):  
Pyroglutamic Acid ◽  
Efficient Synthesis ◽  
Acid Esters

Enantioselective Construction of Alkylated Centers

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Conjugate Addition ◽  
Enantioselective Hydrogenation ◽  
Harvard University ◽  
Grignard Reagents ◽  
Stereogenic Centers ◽  
The University ◽  
Stereogenic Center ◽  
Quaternary Stereogenic Centers ◽  
Peptide Catalyst ◽  
Acid Esters

Unsaturated half acid esters such as 1 are readily prepared by Stobbe condensation between dialkyl succinate and an aldehyde. Johannes G. de Vries of DSM and Floris P. J. T. Rutjes of Radboud University Nijmegen observed (Adv. Synth. Catal. 2008, 350, 85) that these acids were excellent substrates for enantioselective hydrogenation. Kazuaki Kudo of the University of Tokyo designed (Organic Lett. 2008, 10, 2035) a resin bound peptide catalyst for the transfer reduction of unsaturated aldehydes such as 3 , using 4 as the net H2 donor. Note that 5 was produced with high enantiocontrol from 3 that was a ~ 2:1 mixture of geometric isomers. Motomu Kanai and Masakatsu Shibasaki of the University of Tokyo devised (J. Am. Chem. Soc. 2008, 130, 6072) a chiral Gd catalyst that mediated the conjugate cyanation of enones such as 6 with high ee. Eric N. Jacobsen of Harvard University prepared (Angew. Chem. Int. Ed. 2008, 47, 1762) a dimeric Al salen catalyst that showed improved activity over the monomeric catalysts. Even congested imides such as 8 could be cyanated efficiently, delivering alkylated quaternary stereogenic centers. Takahiro Nishimura and Tamio Hayashi of Kyoto University optimized (J. Am. Chem. Soc. 2008, 130, 1576) the Rh*-catalyzed enantioselective conjugate addition of silyl acetylenes to enones such as 10, to give 12. Adriaan J. Minnaard and Ben L. Feringa of the University of Groningen devised (Angew. Chem. Int. Ed. 2008, 47, 398) conditions for the enantioselective 1,6-conjugate addition of alkyl Grignard reagents to diene esters such as the inexpensive ethyl sorbate 14. The product 16 incorporated, in addition to the newly formed stereogenic center, a geometrically defined E alkene. William S. Bechara and André B. Charette of the Université de Montréal found (Organic Lett. 2008, 10, 2315) that alkyl Grignard reagents could be induced to add with high enantioselectivity to pyridyl sulfones such as 17. In a different approach, Gregory C. Fu of MIT developed (J. Am. Chem. Soc. 2008, 130, 3302; J. Am. Chem. Soc. 2008, 130, 2756) conditions for the enantioselective alkenylation of racemic bromo esters such as 19, The latter reference is to the analogous enantioselective coupling of organozinc bromides with racemic allylic chlorides.

Efficient Synthesis of Cyclopropanecarboxylic Acid Esters Starting from the Conjugate Addition of Lithium Ester Enolates to 1-Chlorovinyl p-Tolyl ­Sulfoxides

Synlett ◽  
2013 ◽  
Vol 24 (04) ◽  
pp. 483-486 ◽  
Author(s):  
Tsuyoshi Satoh ◽  
Tsutomu Kimura ◽  
Yoshiaki Hattori ◽  
Hitoshi Momochi ◽  
Nobuhito Nakaya
Keyword(s):  
Conjugate Addition ◽  
Efficient Synthesis ◽  
Cyclopropanecarboxylic Acid ◽  
Acid Esters
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