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

[31] Synthesis of Optically Active α-Trifluoromethylamines by Rearrangement of β-Amino-α-trifluoromethyl Alcohols
Neouchy, Zeina
Pardo, Domingo Gomez
Cossy, Janine
[J]. ORGANIC LETTERS, 2018, 20 (19) : 6017 - 6021
[32] Iron-Catalyzed Carboamination of Olefins: Synthesis of Amines and Disubstituted β-Amino Acids
Qian, Bo
Chen, Shaowei
Wang, Ting
Zhang, Xinhao
Bao, Hongli
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (37) : 13076 - 13082
[33] Stereodivergent Synthesis of α,α-Disubstituted α-Amino Acids via Synergistic Cu/Ir Catalysis
Wei, Liang
Zhu, Qiao
Xu, Shi-Ming
Chang, Xin
Wang, Chun-Jiang
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (04) : 1508 - 1513
[34] Diastereoselective amidoallylation of glyoxylic acid with chiral tert-butanesulfinamide and allylboronic acid pinacol esters: efficient synthesis of optically active γ,δ-unsaturated α-amino acids
Sugiyama, Shigeo
Imai, Saori
Ishii, Keitaro
[J]. TETRAHEDRON-ASYMMETRY, 2013, 24 (18) : 1069 - 1074
[35] Advances in the synthesis of α-quaternary α-ethynyl α-amino acids
Boibessot, Thibaut
Benimelis, David
Meffre, Patrick
Benfodda, Zohra
[J]. AMINO ACIDS, 2016, 48 (09) : 2081 - 2101
[36] Synthesis of optically active α-(nonafluoro-tert-butoxy)carboxylic acids
Csoka, Tamas
Nemes, Aniko
Szabo, Denes
[J]. TETRAHEDRON LETTERS, 2013, 54 (13) : 1730 - 1733
[37] Synthesis of Enantioenriched α-Deuterated α-Amino Acids Enabled by an Organophotocatalytic Radical Approach
Ji, Peng
Zhang, Yueteng
Dong, Yue
Huang, He
Wei, Yongyi
Wang, Wei
[J]. ORGANIC LETTERS, 2020, 22 (04) : 1557 - 1562
[38] A New Strategy for the Synthesis of Optically Pure β-Fluoroalkyl β-Amino Acid Derivatives
Fustero, Santos
del Pozo, Carlos
Catalan, Silvia
Aleman, Jose
Parra, Alejandro
Marcos, Vanesa
Garcia Ruano, Jose Luis
[J]. ORGANIC LETTERS, 2009, 11 (03) : 641 - 644
[39] Catalytic Enantioselective Michael Addition of α-Aryl-α-Isocyanoacetates to Vinyl Selenone: Synthesis of α,α-Disubstituted α-Amino Acids and (+)- and (-)-Trigonoliimine A
Buyck, Thomas
Wang, Qian
Zhu, Jieping
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (48) : 12714 - 12718
[40] Access to α,α-Disubstituted Disilylated Amino Acids and Their Use in Solid-Phase Peptide Synthesis
Fanelli, Roberto
Salah, Khoubaib Ben Haj
Inguimbert, Nicolas
Didierjean, Claude
Martinez, Jean
Cavelier, Florine
[J]. ORGANIC LETTERS, 2015, 17 (18) : 4498 - 4501

← 1 2 3 4 5 →