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Search for "β-amino acid" in Full Text gives 34 result(s) in Beilstein Journal of Organic Chemistry.
Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles
Beilstein J. Org. Chem. 2011, 7, 824–830, doi:10.3762/bjoc.7.94
- methodology, we demonstrated that the homoallylic amine products could be readily converted to synthetically useful building blocks, such as β-amino acids (Scheme 4). N-Boc-protection of the primary amine 12 followed by ozonolysis under Marshall’s conditions [40] yielded the β-amino acid derivative 24. The
- cyclic amine 19 was subjected to analogous reaction conditions to form the tetrahydrofuran β-amino acid derivative 26. Conclusion We have developed a method for the one-pot simultaneous hydrozirconation of allenes and nitriles to yield allylic zirconocenes and N-zirconoimines, respectively. These
- to depend on the allene substitution. The intramolecular variant of this reaction was used to prepare 3-aminotetrahydrofurans and 3-aminotetrahydropyrans, and these addition products can subsequently be transformed into synthetically valuable β-amino acid building blocks. Coupling constant analysis
Asymmetric synthesis of tertiary thiols and thioethers
Beilstein J. Org. Chem. 2011, 7, 582–595, doi:10.3762/bjoc.7.68
- a variety of thiols to a range of nitroalkenes 49 proceeds to give 50 and hence 51 in good yield and good enantioselectivity (Scheme 19). α-Arylthio-β-amino acid 54 was prepared from Michael adduct 52 in three steps (Scheme 20) in good yield and with full conservation of enantiomeric purity. Palomo
- of enone 46. Organocatalytic conjugate addition to nitroalkenes 49. Preparation of β-amino acid 54. Sulfur migration within oxazolidine-2-thiones 56. Preparation of thiols 62 by self-regeneration of stereocentres. Synthesis of (5R)-thiolactomycin. Preparation of tertiary thiols and thioethers via α
An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals
Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57
- of glucagon release. Consequently, insulin secretion increases leading to decreased blood glucose levels in diabetes type II patients. Structurally, this novel antihyperglycaemic consists of a fluorinated β-amino acid which is coupled to a trifluoromethylated triazolopiperazine (Scheme 55). In SAR
α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines
Beilstein J. Org. Chem. 2010, 6, 978–983, doi:10.3762/bjoc.6.110
- an entry to a biologically important β-amino acid mimic class. Aziridines 1h–j. Proposed aziridinyl anion induced N- to C-phosphonyl migration. Selected previously observed N- to C-phosphorous migrations [17][18][21]. Partial N- to C-migration with N-diphenylphosphinylaziridine 10 [24]. Synthesis and
Oxalyl retro-peptide gelators. Synthesis, gelation properties and stereochemical effects
Beilstein J. Org. Chem. 2010, 6, 945–959, doi:10.3762/bjoc.6.106
- centers are denoted corresponding to that of oxalamide α- and β-amino acid, respectively, as depicted in Scheme 1). Compared to the previously studied bis(amino acid)-oxalamide gelators (Figure 1), the retro-dipeptidic gelators, in addition to the oxalamide hydrogen bonding unit, also contain two peptidic
Synthesis of glycosylated β3-homo-threonine conjugates for mucin-like glycopeptide antigen analogues
Beilstein J. Org. Chem. 2010, 6, No. 47, doi:10.3762/bjoc.6.47
- carbohydrate antigens (TACA) have proven to be important target structures for the development of molecularly defined anti-cancer vaccines. The strategic incorporation of β-amino acid building blocks into such mucin-type sequences offers the potential to create pseudo-glycopeptide antigens with improved
- α/β-peptides adopt stable secondary structures closely related to those of natural α-peptides [21][22]. Moreover, inclusion of a single β-amino acid into an α-peptidic sequence already augments local and/or general stability against proteolytic degradation in vitro and in vivo; thus enabling the
The C–F bond as a conformational tool in organic and biological chemistry
Beilstein J. Org. Chem. 2010, 6, No. 38, doi:10.3762/bjoc.6.38
- . This concept is elegantly illustrated by the diastereoisomeric β-peptides 66 and 67 (Figure 18) [56]. The β-amino acid sequence of 66 and 67 is known to promote the formation of a left-handed helix and this helical conformation can be either reinforced or destabilised by a fluorine substituent. In the
2-Phenyl- tetrahydropyrimidine- 4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids
Beilstein J. Org. Chem. 2009, 5, No. 43, doi:10.3762/bjoc.5.43
- , Universitätsstr. 25, 33615 Bielefeld, Germany 10.3762/bjoc.5.43 Abstract Novel procedures have been developed to condense benzaldehyde effectively with β-amino acid amides to cyclic benzyl aminals. Double carbamate protection of the heterocycle resulted in fully protected chiral β-alanine derivatives. These
- , this structural modification would facilitate a final release of the β2-amino acid by hydrogenolysis of all remaining benzyl-type N-protective groups. Results and Discussion Cyclocondensation of benzaldehyde and β-amino acid amides to 2-phenyl-tetrahydropyrimidine-4(1H)-ones is problematic, since
The oxanorbornene approach to 3-hydroxy, 3,4-dihydroxy and 3,4,5-trihydroxy derivatives of 2-aminocyclohexanecarboxylic acid
Beilstein J. Org. Chem. 2006, 2, No. 9, doi:10.1186/1860-5397-2-9
- afforded the trans β-amino acid derivative 22 as established by NMR experiments. Having prepared the 4,5-cis diol, we turned our attention to the synthesis of the corresponding trans diols. These could be prepared by simple hydrolytic cleavage of epoxides 10–13. In line with this plan, treatment of 12 with
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