Enantio- and diastereoselective addition of cyclohexylMeldrum's acid to β- and α,β-disubstituted nitroalkenesvia N-sulfinyl urea catalysis

2012 ◽  
Vol 3 (1) ◽  
pp. 121-125 ◽  
Author(s):  
Kyle L. Kimmel ◽  
Jimmie D. Weaver ◽  
Jonathan A. Ellman
Keyword(s):  
Diastereoselective Addition ◽  
Urea Catalysis

ChemInform Abstract: Enantio- and Diastereoselective Addition of Thioacetic Acid to Nitroalkenes via N-Sulfinyl Urea Catalysis.

ChemInform ◽  
2012 ◽  
Vol 43 (30) ◽  
pp. no-no
Author(s):  
Kyle L. Kimmel ◽  
MaryAnn T. Robak ◽  
Stephen Thomas ◽  
Melissa Lee ◽  
Jonathan A. Ellman
Keyword(s):  
Thioacetic Acid ◽  
Diastereoselective Addition ◽  
Urea Catalysis

Enantio- and diastereoselective addition of thioacetic acid to nitroalkenes via N-sulfinyl urea catalysis

Tetrahedron ◽  
2012 ◽  
Vol 68 (12) ◽  
pp. 2704-2712 ◽  
Author(s):  
Kyle L. Kimmel ◽  
MaryAnn T. Robak ◽  
Stephen Thomas ◽  
Melissa Lee ◽  
Jonathan A. Ellman
Keyword(s):  
Thioacetic Acid ◽  
Diastereoselective Addition ◽  
Urea Catalysis

O-AcylTEMPOs, a Modified and Fundamental, but Unexplored Carboxylic Derivative: Recent Progress in Synthetic Applications

2019 ◽  
Vol 23 (19) ◽  
pp. 2102-2121
Author(s):  
Hiroyuki Kawafuchi ◽  
Lijian Ma ◽  
Md Imran Hossain ◽  
Tsutomu Inokuchi
Keyword(s):  
Organic Synthesis ◽  
Recent Progress ◽  
Knoevenagel Condensation ◽  
Acid Synthesis ◽  
Amino Acid Synthesis ◽  
Electrophilic Amination ◽  
Weinreb Amides ◽  
Anionic Species ◽  
Diastereoselective Addition ◽  
Carbonyl Function

O-Acylated 2,2,6,6-tetramethylpiperidine-N-oxyls (abbr. O-AcylTEMPOs) are easily available and stable carboxylic derivatives, but their utility in organic synthesis is unexplored in contrast to analogues, such as the N-methoxy-N-methylamides, known as Weinreb amides. Especially, the O–N unit of the O-acylTEMPOs dictates a fairly electronwithdrawing character for the carbonyl function. This enhances the reactivity and stability of the resulting enolate ions. Accordingly, O-acylTEMPOs allow various transformations and this review encompasses seven topics: (1) Reactivity of O-acylTEMPOs towards nucleophiles and chemoselective transformations, (2) Reactivity of anionic species derived from O-acylTEMPOs, (3) E-Selective Knoevenagel condensation of acetoacetylTEMPOs and synthesis of furans, (4) Electrocyclization of 2,4-dienones derived from acetoacetic derivatives and 2-substituted enals, (5) Diastereoselective addition of amide anion to O-(2-alkenoyl)TEMPOs and β-amino acid synthesis, (6) Thermolysis of O-acylTEMPOs, and (7) Applications for Umpolung reactions using O-benzoylTEMPOs, useful for the electrophilic amination of alkenes and alkynes.

Diastereoselective Addition of Organometallic Reagents to Nor-Ephedrine-Derived 2-Acyl-N-Tosyl-Oxazolidines

Synlett ◽  
1995 ◽  
Vol 1995 (01) ◽  
pp. 71-73 ◽  
Author(s):  
Giovanni Poli ◽  
Elisa Maccagni ◽  
Leonardo Manzoni ◽  
Tullio Pilati ◽  
Carlo Scolastico
Keyword(s):  
Organometallic Reagents ◽  
Diastereoselective Addition

Umpolung Synthesis of Vicinal Diamines: Diastereoselective Addition of 2-Azaallyl Anions to Davis–Ellman’s Imines

2018 ◽  
Vol 20 (17) ◽  
pp. 5423-5426 ◽  
Author(s):  
Leleti Rajender Reddy ◽  
Sharadsrikar Kotturi ◽  
Rajesh Shenoy ◽  
Kumara Swamy Nalivela ◽  
Chirag Patel ◽  
...  
Keyword(s):  
Diastereoselective Addition ◽  
Vicinal Diamines
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