Gold-catalyzed synthesis of enantioenriched furfurylamines from amino acids. Issue 15 (31st August 2015)

• Record Type: Journal Article
• Authors: Guieu, Benjamin; Le Roch, Myriam; David, Michèle; Gouault, Nicolas
• Is Part Of: Tetrahedron, asymmetry. Volume 26:Issue 15/16(2015)
• Page Start: 868
• Page End: 875
• Publication Date: 2015-08-31
• Subjects: Asymmetry (Chemistry) -- Periodicals; 547.005
• DOI: 10.1016/j.tetasy.2015.06.014
• Languages: English
• ISSNs: 0957-4166

Abstract

Graphical abstract: Abstract: A convenient gold-catalyzed asymmetric synthesis of polysubstituted furfurylamines starting from amino acids has been achieved. The cyclization proceeded under mild conditions and generally provided the furan or iodofuran derivatives in good to excellent yields and with high enantiomeric excess. Iodofurans were validated as good intermediates for classical organometallic coupling reactions. Abstract : tert- Butyl ( S ) - (2-(benzyloxy)-1-(5-ethylfuran-2-yl)ethyl)carbamate: C20 H27 NO4 [ α ]D 22 = −35.1 ( c 1.00, CH2 Cl2 ) Source of chirality: N -Boc-l -serine Absolute configuration: ( S ) Abstract : tert- Butyl ( R )-(2-(phenyl)-1-(5-propylfuran-2-yl)ethyl)carbamate: C20 H27 NO3 [ α ]D 22 = +43.4 ( c 1.07, CH2 Cl2 ) Source of chirality: N -Boc-d -phenylalanine Absolute configuration: ( R ) Abstract : tert- Butyl ( S ) - (2-(benzyloxy)-1-(5-ethyl-4-iodofuran-2-yl)ethyl)carbamate: C20 H26 INO4 [ α ]D 22 = −36.5 ( c 1.02, CH2 Cl2 ) Source of chirality: N -Boc-l -serine Absolute configuration: ( S ) Abstract : tert- Butyl ( R )-(1-(4-iodo-5-propylfuran-2-yl)-2-phenylethyl)carbamate: C20 H26 INO3 [ α ]D 22 = +38.3 ( c 1.08, CH2 Cl2 ) Source of chirality: N -Boc-d -phenylalanine Absolute configuration: ( R ) Abstract : ( S )-2-(4-Iodo-5-phenylfuran-2-yl)pyrrolidine-1-carboxylic acid tert -butyl ester: C19 H22 INO3 [ α ]D 22 = −101.0 ( c 1.04, CH2 Cl2 ) Source of chirality: N -Boc-l -proline Absolute configuration: ( S ) Abstract : tert- Butyl ( S )-(2-(benzyloxy)-1-(5-ethyl-4-(4-fluorophenyl)furan-2-yl)ethyl)carbamate: C26 H30 FNO4 [ α ]D 22 = −36.4 ( c 0.99, CH2 Cl2 ) Source of chirality: N -Boc-l -serine Absolute configuration: ( S ) Abstract : tert- Butyl ( R )-(1-(4-(4-fluorophenyl)-5-propylfuran-2-yl)-2-phenylethyl)carbamate: C26 H30 FNO3 [ α ]D 22 = +36.6 ( c 1.00, CH2 Cl2 ) Source of chirality: N -Boc-d -phenylalanine Absolute configuration: ( R ) Abstract : ( S )-2-(4-(4-(( tert -Butoxycarbonyl)amino)phenyl)-5-phenylfuran-2-yl)pyrrolidine-1-carboxylic acid tert -butyl ester: C30 H36 N2 O5 [ α ]D 22 = −86.3 ( c 0.91, CH2 Cl2 ) Source of chirality: N -Boc-l -proline Absolute configuration: ( S ) Abstract : ( R, E )-3-(5-(1-(( tert -Butoxycarbonyl)amino)-2-phenylethyl)-2-propylfuran-3-yl)acrylic acid methyl ester: C24 H31 NO5 [ α ]D 22 = +31.7 ( c 0.94, CH2 Cl2 ) Source of chirality: N -Boc-d -phenylalanine Absolute configuration: ( R ) Abstract : ( R )-(2-Phenyl-1-(4-(phenylethynyl)-5-propylfuran-2-yl)ethyl)carbamic acid tert -butyl ester: C28 H31 NO3 [ α ]D 22 = +34.2 ( c 1.04, CH2 Cl2 ) Source of chirality: N -Boc-d -phenylalanine Absolute configuration: ( R ) Abstract : ( S )-2-(4(( tert -Butoxycarbonyl)amino)-5-phenylfuran-2-yl)pyrrolidine-1-carboxylic acid tert -butyl ester: C24 H32 N2 O5 [ α ]D 22 = −89.0 ( c 1.23, CH2 Cl2 ) Source of chirality: N -Boc-l -proline Absolute configuration: ( S ) Abstract : ( S )-(1-(5-Ethylfuran-2-yl)-2-hydroxyethyl)carbamic acid tert -butyl ester: C13 H21 NO4 [ α ]D 22 = −51.1 ( c 1.00, CH2 Cl2 ) Source of chirality: N -Boc-l -serine Absolute configuration: ( S ) Abstract : ( S ) - (1-(5-Ethyl-4-(4-fluorophenyl)furan-2-yl)-2-hydroxyethyl)carbamic acid tert -butyl ester: C19 H24 FNO4 [ α ]D 22 = −49.4 ( c 0.50, CH2 Cl2 ) Source of chirality: N -Boc-l -serine Absolute configuration: ( S ) Abstract : ( S ) - 2-Amino-2-(5-ethylfuran-2-yl)ethan-1-ol, hydrochloride: C8 H14 ClNO2 [ α ]D 22 = −16.2 ( c 0.50, CH3 OH) Source of chirality: N -Boc-l -serine Absolute configuration: ( S )