Development of a stereoselective Ugi reaction starting from an oxanorbornene β-amino acid derivative

被引：20

作者：

Banfi, Luca ^{[1
]}

Basso, Andrea ^{[1
]}

Chiappe, Cinzia ^{[2
]}

De Moliner, Fabio ^{[3
]}

Riva, Renata ^{[1
]}

Sonaglia, Lorenzo ^{[1
]}

机构：

[1] Univ Genoa, Dipartimento Chim & Chim Ind, Genoa, Italy

[2] Univ Pisa, Dipartimento Chim & Chim Ind, Pisa, Italy

[3] Univ Arizona, Dept Pharmacol & Toxicol, Tucson, AZ 85721 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 19期

关键词：

ASYMMETRIC-SYNTHESIS; ALPHA-AMINO; AUXILIARY; POLARITY;

D O I：

10.1039/c2ob25060h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have synthesised a novel oxanorbornene beta-aminoacid derivative and employed it in a stereoselective Ugi reaction. Hypothesis regarding the mechanism taking place during the reaction have been made and validated through the determination of the relative and absolute configuration of the Ugi adducts. Use of the correct choice of solvents can increase stereoselection. The resulting bicyclic peptidomimetics can be used as a novel class of pluripotent substrates to be elaborated according to the synthetic strategies previously elaborated in our laboratories.

引用

页码：3819 / 3829

页数：11

共 26 条

[1] Synthesis of 3-nitropropanol homologues [J].

Addo, JK ;

Teesdale-Spittle, P ;

Hoberg, JO .

SYNTHESIS-STUTTGART, 2005, (12) :1923-1925

[2] Nitroaldol (Henry) reaction catalyzed by Amberlyst A-21 as a far superior heterogeneous catalyst. [J].

Ballini, R ;

Bosica, G ;

Forconi, P .

TETRAHEDRON, 1996, 52 (05) :1677-1684

[3] A novel highly selective chiral auxiliary for the asymmetric synthesis of L- and D-α-amino acid derivatives via a multicomponent Ugi reaction [J].

Basso, A ;

Banfi, L ;

Riva, R ;

Guanti, G .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :575-579

[4] U-4C-3CR versus U-5C-4CR and stereochemical outcomes using suitable bicyclic β-amino acid derivatives as bifunctional components in the Ugi reaction [J].

Basso, A ;

Banfi, L ;

Riva, R ;

Guanti, G .

TETRAHEDRON LETTERS, 2004, 45 (03) :587-590

[5] Preparation of optically pure fused polycyclic scaffolds by Ugi reaction followed by olefin and enyne metathesis [J].

Basso, Andrea ;

Banfi, Luca ;

Riva, Renata ;

Guanti, Giuseppe .

TETRAHEDRON, 2006, 62 (37) :8830-8837

[6] A Marriage of Convenience: Combining the Power of Isocyanide-Based Multicomponent Reactions with the Versatility of (Hetero)norbornene Chemistry [J].

Basso, Andrea ;

Banfi, Luca ;

Riva, Renata .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (10) :1831-1841

[7] Straightforward stereoselective synthesis of polyfunctionalized cyclohexenols using a multicomponent approach [J].

Basso, Andrea ;

Banfi, Luca ;

Guanti, Giuseppe ;

Riva, Renata .

TETRAHEDRON, 2010, 66 (13) :2390-2397

[8] An alkaloid-mediated desymmetrization of meso-anhydrides via a nucleophilic ring opening with benzyl alcohol and its application in the synthesis of highly enantiomerically enriched β-amino acids [J].

Bolm, C ;

Schiffers, I ;

Atodiresei, I ;

Hackenberger, CPR .

TETRAHEDRON-ASYMMETRY, 2003, 14 (22) :3455-3467

[9] Asymmetric synthesis of the putative structure of (-)-oryzoxymycin [J].

Bunnage, ME ;

Ganesh, T ;

Masesane, IB ;

Orton, D ;

Steel, PG .

ORGANIC LETTERS, 2003, 5 (03) :239-242

[10] Polarity, Viscosity, and Ionic Conductivity of Liquid Mixtures Containing [C4C1im][Ntf2] and a Molecular Component [J].

Canongia Lopes, J. N. ;

Gomes, Margarida F. Costa ;

Husson, Pascale ;

Padua, Agilio A. H. ;

Rebelo, Luis Paulo N. ;

Sarraute, Sabine ;

Tariq, Mohammad .

JOURNAL OF PHYSICAL CHEMISTRY B, 2011, 115 (19) :6088-6099

← 1 2 3 →