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

[21] Recent Advances in the Synthesis of Fluorinated Amino Acids
Qiu, Xiao-Long
Qing, Feng-Ling
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (18) : 3261 - 3278
[22] Synthesis of Optically Active β-Amino Alcohols by Asymmetric Transfer Hydrogenation of α-Amino Ketones
Xu, Zhou
Zhu, Songlei
Liu, Yongmin
He, Ling
Geng, Zhicong
Zhang, Yawen
SYNTHESIS-STUTTGART, 2010, (05): : 811 - 817
[23] Lewis Acid Promoted Highly Diastereoselective Petasis Borono-Mannich Reaction: Efficient Synthesis of Optically Active β,γ-Unsaturated α-Amino Acids
Li, Yi
Xu, Ming-Hua
ORGANIC LETTERS, 2012, 14 (08) : 2062 - 2065
[24] Catalytic enantioselective aza-Diels-Alder reactions of imines -: An approach to optically active nonproteinogenic α-amino acids
Yao, SL
Saaby, S
Hazell, RG
Jorgensen, KA
CHEMISTRY-A EUROPEAN JOURNAL, 2000, 6 (13) : 2435 - 2448
[25] Facile Approach to Optically Active α-Alkylidene-β-amino Esters by Thermal Overman Rearrangement
Lee, Sung Il
Moon, Soon Young
Hwang, Geum-Sook
Ryu, Do Hyun
ORGANIC LETTERS, 2010, 12 (14) : 3234 - 3237
[26] Design and synthesis of chiral α,α-disubstituted amino acids and conformational study of their oligopeptides
Tanaka, Masakazu
CHEMICAL & PHARMACEUTICAL BULLETIN, 2007, 55 (03) : 349 - 358
[27] Synthesis and selected transformations of optically active cyclopentenyl sulfoxides: New approach to optically active cyclopentenones
Midura, W. H.
Krysiak, J.
Wieczorek, M. W.
Filipczak, A.
POLISH JOURNAL OF CHEMISTRY, 2007, 81 (02) : 211 - 223
[28] Stereocontrolled routes to β,β′-disubstituted α-amino acids
Michaux, Julien
Niel, Gilles
Campagne, Jean-Marc
CHEMICAL SOCIETY REVIEWS, 2009, 38 (07) : 2093 - 2116
[29] The preparation of optically active α-amino 4H-[1,2,4]oxadiazol-5-ones from optically active α-amino acids
Mangette, John E.
Johnson, Matthew R.
Le, Van-Duc
Shenoy, Rajesh A.
Roark, Howard
Stier, Michael
Belliotti, Thomas
Capiris, Thomas
Guzzo, Peter R.
TETRAHEDRON, 2009, 65 (46) : 9536 - 9541
[30] Chemoenzymatic synthesis of optically active 1,2-disubstituted ferrocenes with planar chirality
Merabet-Khellasi, Mounia
Aribi-Zouioueche, Louisa
Riant, Olivier
TETRAHEDRON-ASYMMETRY, 2009, 20 (12) : 1371 - 1377

← 1 2 3 4 5 →