Transition-Metal-Free Cyclopropanation of 2-Aminoacrylates with N-Tosylhydrazones: A General Route to Cyclopropane α-Amino Acid with Contiguous Quaternary Carbon Centers

2016 ◽  
Vol 18 (6) ◽  
pp. 1470-1473 ◽  
Author(s):  
Chuanle Zhu ◽  
Jiawei Li ◽  
Pengquan Chen ◽  
Wanqing Wu ◽  
Yanwei Ren ◽  
...  
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Quaternary Carbon ◽  
Metal Free ◽  
Carbon Centers

ChemInform Abstract: Transition-Metal-Free Decarboxylation of Dimethyl Malonate: An Efficient Construction of α-Amino Acid Esters Using TBAI/TBHP.

ChemInform ◽  
2015 ◽  
Vol 46 (29) ◽  
pp. no-no
Author(s):  
Jie Zhang ◽  
Ying Shao ◽  
Yaxiong Wang ◽  
Huihuang Li ◽  
Dongmei Xu ◽  
...  
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Amino Acid Esters ◽  
Dimethyl Malonate ◽  
Metal Free ◽  
Efficient Construction ◽  
Acid Esters

scholarly journals Metal-Free–Catalyzed Oxidative Trimerization of Indoles Using NaNO2 to Construct Quaternary Carbon Centers: Synthesis of 2-(1H-Indol-3-yl)-2,3′-biindolin-3-ones

2014 ◽  
Vol 44 (15) ◽  
pp. 2215-2221 ◽  
Author(s):  
Jun Xue ◽  
Yunhong Bao ◽  
Wenbing Qin ◽  
Jiayi Zhu ◽  
Yubo Kong ◽  
...  
Keyword(s):  
Quaternary Carbon ◽  
Metal Free ◽  
Carbon Centers

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.

Transition-metal-free decarboxylation of dimethyl malonate: an efficient construction of α-amino acid esters using TBAI/TBHP

2015 ◽  
Vol 13 (13) ◽  
pp. 3982-3987 ◽  
Author(s):  
Jie Zhang ◽  
Ying Shao ◽  
Yaxiong Wang ◽  
Huihuang Li ◽  
Dongmei Xu ◽  
...  
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Amino Acid Esters ◽  
Dimethyl Malonate ◽  
Metal Free ◽  
New Strategy ◽  
Efficient Construction ◽  
Acid Esters

A new strategy has been developed for the synthesis of α-amino acid esters via a tandem hydrolysis/decarboxylation/nucleophilic substitution using TBAI/TBHP.

Transition metal-free aerobic oxidative cleavage of the C–N bonds of α-amino esters

2019 ◽  
Vol 6 (23) ◽  
pp. 3854-3858
Author(s):  
Shenpeng Tan ◽  
Feng Li ◽  
Soojun Park ◽  
Sanghee Kim
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Metal Catalysts ◽  
Oxidative Cleavage ◽  
Amino Acid Derivatives ◽  
Metal Free ◽  
Amino Esters

A base-mediated aerobic oxidative cleavage of α-amino esters involving a hydroperoxide intermediate was reported, which represents the first example of the cleavage of the α-C–N bonds of amino acid derivatives without the aid of metal catalysts.

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