101386-28-1Relevant articles and documents
A Novel Class of 7-Membered Heterocyclic Compounds
Bauer, Adriano,Borsos, Eszter,Maulide, Nuno
supporting information, p. 3971 - 3974 (2020/05/25)
The work presented herein describes the synthesis of a formerly inaccessible class of heterocyclic compounds. The reaction relies on α-phthalimido-amides, which are readily prepared from amino acids in 2 simple reactions steps. Under amide activation conditions in which classical keteniminium ions are not formed, the nitrile solvent is incorporated into the new fused 7-membered ring system. Due to the absence of a keteniminium intermediate, the stereogenic information in the α-position is fully retained.
Bioinspired Deamination of α-Amino Acid Derivatives Catalyzed by a Palladium/Nickel Complex
Deng, Gongtao,Chen, Jie,Sun, Wangbin,Bian, Kehan,Jiang, Yaojia,Loh, Teck-Peng
supporting information, p. 3900 - 3905 (2018/09/12)
An efficient bioinspired deamination method of both natural and unnatural amino acid derivatives has been developed. This method provides easy access to a wide variety of useful α, β-unsaturated carbonyl compounds. The reaction is realized with two transition metal catalysts (palladium and Nickel) in-easy handling procedure. A possible reaction pathway is also proposed and the control experiments support the involvement of the palladium-catalyzed inert sp3 C?H activation as one of the key steps. (Figure presented.).
Synthesis of Quaternary α-Fluorinated α-Amino Acid Derivatives via Coordinating Cu(II) Catalytic α-C(sp3)-H Direct Fluorination
Wei, Qiang,Ma, Yao,Li, Li,Liu, Qingfei,Liu, Zijie,Liu, Gang
supporting information, p. 7100 - 7103 (2018/11/24)
A coordinating, copper-catalyzed direct α-C(sp3)-H fluorination method has been developed to prepare vital quaternary α-fluorinated α-amino acid derivatives. A Cu(II) catalytic SET oxidative addition mechanism is proposed, involving a key fluoride-coupled Cu(II) charge transfer complex. The protocol can tolerate a rich variety of α-amino acids, for which the auxiliary group is removed in high yield and substituted for the direct preparation of dipeptide derivatives with detachable, single absolute configurations of the target compounds.
Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization
O'Duill, Miriam L.,Matsuura, Rei,Wang, Yanyan,Turnbull, Joshua L.,Gurak, John A.,Gao, De-Wei,Lu, Gang,Liu, Peng,Engle, Keary M.
supporting information, p. 15576 - 15579 (2017/11/14)
Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselective remote hydrocarbofunctionalization of several synthetically useful alkene-containing substrate classes, including 4-pentenoic acids, allylic alcohols, homoallyl amines, and bis-homoallylamines, under Pd(II) catalysis. In conjunction with previous findings, we demonstrate regiodivergent hydrofunctionalization of 3-butenoic acid derivatives to afford either Markovnikov or anti-Markovnikov addition products depending on directing group choice. Preliminary mechanistic and computational data are presented to support the proposed catalytic cycle.
4-Amino-2-alkyl-butyramides as small molecule CCR2 antagonists with favorable pharmacokinetic properties
Butora, Gabor,Morriello, Gregori J.,Kothandaraman, Shankaran,Guiadeen, Deodialsingh,Pasternak, Alexander,Parsons, William H.,MacCoss, Malcolm,Vicario, Pasquale P.,Cascieri, Margaret A.,Yang, Lihu
, p. 4715 - 4722 (2007/10/03)
A systematic examination of the central aromatic portion of the lead (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-(4-fluorophenyl)-4-(1′H-spiro[indene-1,4′-piperidin]-1′-yl)butanamide (9) led to the discovery of a novel class of CCR2 receptor antagonists, which carry small alicyclic groups such as cyclopropyl, cylobutyl, or cyclopropylmethyl attached at C2 of the carbon backbone. The most potent compound discovered, namely (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-cyclopropyl-4-[(1R,3′R)-3′-methyl-1′H-spiro[indene-1,4′-piperidin]-1′-yl]butanamide (29), showed very high binding affinity (IC50 = 4 nM, human monocyte) and excellent selectivity toward other related chemokine receptors. The excellent pharmacokinetic profile of this new lead compound allows for extensive in vivo evaluation.
Synthesis of Cyclopropyl Amino Acid Derivatives
Easton, Christopher J.,Tan, Eng Wui,Ward, Caroline M.
, p. 395 - 402 (2007/10/02)
Derivatives of α,β-methanovaline, α,β-methanophenylalanine and β-methyl-α,β-methanoalanine have been prepared by regioselective side-chain functionalization of suitably protected amino acid derivatives, followed by cyclization with either sodium hydride or 1,8-diazabicycloundec-7-ene.The approach used in this work illustrates a method for the synthesis of cyclopropyl amino acid derivatives which is complementary to existing procedures.
