94480-67-8Relevant academic research and scientific papers
Synthesis of new chiral 2,2′-bipyridine ligands and their application in Copper-catalyzed asymmetric allylic oxidation and cyclopropanation
Malkov, Andrei V.,Pernazza, Daniele,Bell, Mark,Bella, Marco,Massa, Antonio,Teply, Filip,Meghani, Premji,Kocovsky, Pavel
, p. 4727 - 4742 (2007/10/03)
A series of modular bipyridine-type ligands 1 and 3-9 has been synthesized via a de novo construction of the pyridine nucleus. The chiral moieties of these ligands originate from the isoprenoid chiral pool, namely, β-pinene (10 → 1), 3-carene (14 → 3 and 5), 2-carene (28 → 4), α-pinene (43 → 6-8), and dehydropregnenolone acetate (48 → 9), respectively. Copper(I) complexes, derived from these ligands and (TfO)2Cu (1 mol%) upon an in situ reduction with phenylhydrazine, exhibit good enantioselectivity (up to 82% ee) and unusually high reaction rate (typicaly 30 min at room temperature) in allylic oxidation of cyclic olefins (52 → 53). Copper-catalyzed cyclopropanation proceeded with ≤76% enantioselectivity and ～3:1 to 99:1 trans/cis-diastereoselectivity (54 → 55 + 56). The level of the asymmetric induction is discussed in terms of the ligand architecture that controls the stereochemical environment of the coordinated metal.
ELECTROPHILIC ADDITION OF LEAD TETRAACETATE TO 2-CARENE IN AN ACIDIDIC MEDIUM
Arbuzov, B. A.,Isaeva, Z. G.,Belyaeva, M. G.,Ratner, V. V.,Kataeva, O. N.,et al.
, p. 117 - 119 (2007/10/02)
Oxidation of 2-carene by lead tetraacetate in acetic acid afforded p-menth-1(10),2-dien-7-ol, 2-acetyl-6,6-dimethylbicyclohexane, p-menth-2-ene-1α,7-diol, p-menth-1-ene-3β,7-diol, and 2-(m-tolyl)propanol-2.Keywords: oxidation, lead tetraacetate, 2-carene, benzene, acetic acid, medium polarity.
Studies on the Terpenoids and Related Alicyclic Compounds. XXXV. Studies Directed toward a Total Synthesis of Ingenol Esters: Synthesis of the C/D-Ring Moiety of Ingenol Esters from (+)-3-Carene via Tin(IV) Chloride-Promoted Intramolecular Directed Aldol
Satoh, Tsuyoshi,Kaneko, Youhei,Okuda, Teruyoshi,Uwaya, Satoru,Yamakawa, Koji
, p. 3452 - 3460 (2007/10/02)
(+)-(1S,5R,7R)-5,8,8-Trimethylbicyclooctan-3-one (2), which comprises the C/D-ring moiety of ingenol esters (1) and is an important chiral synthon for a total synthesis of ingenol esters from easily available (+)-3-carene (3), was synthesized.Intra
