Mitsunobu Approach to the Synthesis of Optically Active α,α-Disubstituted Amino Acids

被引：73

作者：

Green, Jonathan E. ^{[1
,2
]}

Bender, David M. ^{[2
]}

Jackson, Stona ^{[2
]}

O'Donnell, Martin J. ^{[1
]}

McCarthy, James R. ^{[2
]}

机构：

[1] Indiana Univ Purdue Univ, Dept Chem & Chem Biol, Indianapolis, IN 46202 USA

[2] Eli Lilly & Co, Lilly Corp Ctr, Indianapolis, IN 46285 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 04期

关键词：

ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; ALKYL-ARYL; REAGENT; ALCOHOLS; DESIGN; ETHERS;

D O I：

10.1021/ol802325h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral tertiary alpha-hydroxy esters of known stereochemical configuration were transformed to a-azido esters by Mitsunobu reaction with HN3. Optimization of this reaction was shown to proceed at room temperature with high chemical yield using 1,1-(azodicarbonyl)dipiperidine (ADDP) and trimethylphosphine (PMe3). Complete inversion of configuration was observed at the a-carbon. Several alpha,alpha-disubstituted amino acids were synthesized in high overall chemical yield and optical purity.

引用

页码：807 / 810

页数：4

共 50 条

[41] Catalytic, One-Pot Synthesis of β-Amino Acids from α-Amino Acids. Preparation of α,β-Peptide Derivatives [J].

Saavedra, Carlos ;

Hernandez, Rosendo ;

Boto, Alicia ;

Alvarez, Eleuterio .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (13) :4655-4665

[42] (S)-α-methyl,α-amino acids: a new stereocontrolled synthesis [J].

Balducci, Daniele ;

Lazzari, Ilaria ;

Monari, Magda ;

Piccinelli, Fabio ;

Porzi, Gianni .

AMINO ACIDS, 2010, 38 (03) :829-837

[43] Synthesis of Optically Active Amino Acid Derivatives via Dynamic Kinetic Resolution [J].

Choi, Yoon Kyung ;

Kim, Yunwoong ;

Han, Kiwon ;

Park, Jaiwook ;

Kim, Mahn-Joo .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) :9543-9545

[44] Organocatalytic synthesis of optically active heteroaromatic compounds [J].

Albrecht, Lukasz ;

Ransborg, Lars Krogager ;

Jorgensen, Karl Anker .

CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (06) :1089-1098

[45] Recent developments in the asymmetric synthesis of optically active 2-arylpropanonic acids [J].

Chen, ZL ;

Wu, YL ;

Wu, YK .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2002, 22 (01) :22-32

[46] RETRACTED: Enantioselective Radical Addition to Ketimines: A Synthetic Route Towards α,α-Disubstituted α-Amino Acids (Retracted Article) [J].

Kim, Sang Yoon ;

Kim, Sung Jun ;

Jang, Doo Ok .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (44) :13046-13048

[47] Rearrangement Reactions Leading to Optically Active α,α-Disubstituted Primary Allylamines [J].

Hennum, Martin ;

Odden, Hege Hortemo ;

Gundersen, Lise-Lotte .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (04) :846-860

[48] γ-Amino vinyl sulfoxides in asymmetric synthesis. Synthesis of optically pure α-substituted β-amino nitriles [J].

Alfaro, Ricardo ;

Yuste, Francisco ;

Ortiz, Benjamin ;

Sanchez-Obregon, Ruben ;

Garcia Ruano, Jose L. .

TETRAHEDRON, 2009, 65 (01) :357-363

[49] Asymmetric amino acid synthesis: Mitsunobu reaction on chiral cyanohydrins [J].

Decicco, CP ;

Grover, P .

SYNLETT, 1997, (05) :529-&

[50] Synthesis of new racemic and optically active N-phosphonoalkyl bicyclic ß-amino acids via the kabachnik-fields reaction as potential biologically active compounds [J].

Todorov, Petar T. ;

Pavlov, Nikola D. ;

Shivachev, Boris L. ;

Petrova, Rosica N. ;

Martinez, Jean ;

Naydenova, Emilia D. ;

Calmes, Monique .

HETEROATOM CHEMISTRY, 2012, 23 (02) :123-130

← 1 2 3 4 5 →