Chiral Calcium Complexes as Brønsted Base Catalysts for Asymmetric Addition of α-Amino Acid Derivatives to α,β-Unsaturated Carbonyl Compounds

2007 ◽  
Vol 129 (17) ◽  
pp. 5364-5365 ◽  
Author(s):  
Susumu Saito ◽  
Tetsu Tsubogo ◽  
Shū Kobayashi
Keyword(s):  
Amino Acid ◽  
Carbonyl Compounds ◽  
Amino Acid Derivatives ◽  
Asymmetric Addition ◽  
Base Catalysts ◽  
Calcium Complexes ◽  
Brønsted Base

scholarly journals Arylation and alkenylation of activated alkyl halides using sulfonamides

2020 ◽  
Vol 56 (21) ◽  
pp. 3222-3224
Author(s):  
Stuart Johnson ◽  
Ervin Kovács ◽  
Michael F. Greaney
Keyword(s):  
Amino Acid ◽  
Carbonyl Compounds ◽  
Alkyl Halides ◽  
Amino Acid Derivatives ◽  
Smiles Rearrangement

A variety of quaternary aryl amino acid derivatives can be synthesised using tandem SN2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds.

scholarly journals Directed, Nickel-Catalyzed Umpolung 1,2-Carboamination of Alkenyl Carbonyl Compounds

2018 ◽  
Author(s):  
Vincent van der Puyl ◽  
Joseph Derosa ◽  
Keary Engle
Keyword(s):  
Amino Acid ◽  
Tertiary Amine ◽  
Carbonyl Compounds ◽  
Amino Acid Derivatives ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Two Component ◽  
Directing Group

We report a regioselective, nickel-catalyzed <i>syn</i>-1,2-carboamination of non-conjugated alkenyl carbonyl compounds with <i>O</i>-benzoyl hydroxylamine (N–O) electrophiles and aryl/alkylzinc nucleophiles to afford β- and γ-amino acid derivatives. This method enables preparation of products containing structurally diverse tertiary amine motifs, including heterocycles, and can also be used to form quaternary carbon centers. The reaction takes advantage of a tethered 8-aminoquinoline directing group to control the regiochemical outcome and suppress two-component coupling between the N–O electrophile and organozinc nucleophile.

scholarly journals Directed, Nickel-Catalyzed Umpolung 1,2-Carboamination of Alkenyl Carbonyl Compounds

2018 ◽  
Author(s):  
Vincent van der Puyl ◽  
Joseph Derosa ◽  
Keary Engle
Keyword(s):  
Amino Acid ◽  
Tertiary Amine ◽  
Carbonyl Compounds ◽  
Amino Acid Derivatives ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Two Component ◽  
Directing Group

We report a regioselective, nickel-catalyzed <i>syn</i>-1,2-carboamination of non-conjugated alkenyl carbonyl compounds with <i>O</i>-benzoyl hydroxylamine (N–O) electrophiles and aryl/alkylzinc nucleophiles to afford β- and γ-amino acid derivatives. This method enables preparation of products containing structurally diverse tertiary amine motifs, including heterocycles, and can also be used to form quaternary carbon centers. The reaction takes advantage of a tethered 8-aminoquinoline directing group to control the regiochemical outcome and suppress two-component coupling between the N–O electrophile and organozinc nucleophile.

The Ugi reaction with CF3-carbonyl compounds: effective synthesis of α-trifluoromethyl amino acid derivatives

Tetrahedron ◽  
2008 ◽  
Vol 64 (51) ◽  
pp. 11706-11712 ◽  
Author(s):  
Anton V. Gulevich ◽  
Nikolay E. Shevchenko ◽  
Elisabeth S. Balenkova ◽  
Gerd-Volker Röschenthaler ◽  
Valentine G. Nenajdenko
Keyword(s):  
Amino Acid ◽  
Carbonyl Compounds ◽  
Ugi Reaction ◽  
Amino Acid Derivatives ◽  
Effective Synthesis
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