212066-31-4Relevant articles and documents
Catalytic Asymmetric Intermolecular Cyclopropanation of a Ketone Carbene Precursor by a Ruthenium(II)-Pheox Complex
Chi, Le Thi Loan,Suharto, Agus,Da, Ho Linh,Chanthamath, Soda,Shibatomi, Kazutaka,Iwasa, Seiji
supporting information, p. 951 - 955 (2019/01/25)
The diazo derivative of acetonyl acetate is a useful basic skeleton for the synthesis of cyclopropyl ketones. The intermolecular cyclopropanations of diazo acetoxy acetone with olefins are accomplished by using a novel p-nitro-Ru(II)-diphenyl-Pheox catalyst to give the corresponding optically active cyclopropane derivatives in good yields (up to 95%) with excellent diastereoselectivities (up to 99:1) and enantioselectivities (up to 98% ee). (Figure presented.).
CYCLOPROPANE DERIVATIVE HAVING BACE1 INHIBITING ACTIVITY
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, (2014/02/15)
The present invention relates to compounds of the Formula (I) and (II): wherein each variable is as defined in the specification, pharmaceutically acceptable salts and solvates thereof, as well as use of such compounds as a BACE1 inhibitor. The compounds of the invention are useful as an agent for treating a disease induced by production, secretion and/or deposition of amyloid β protein.
Conformational restriction approach to β-secretase (BACE1) inhibitors III: Effective investigation of the binding mode by combinational use of X-ray analysis, isothermal titration calorimetry and theoretical calculations
Yonezawa, Shuji,Fujiwara, Kenichiro,Yamamoto, Takahiko,Hattori, Kazunari,Yamakawa, Hidekuni,Muto, Chie,Hosono, Motoko,Tanaka, Yoshikazu,Nakano, Toru,Takemoto, Hiroshi,Arisawa, Mitsuhiro,Shuto, Satoshi
, p. 6506 - 6522 (2013/10/22)
For further investigation of BACE1 inhibitors using conformational restriction with sp3 hybridized carbon, we applied this approach to 6-substituted aminopyrimidone derivatives 3 to improve the inhibitory activity by reducing the entropic energy loss upon binding to BACE1. Among eight stereoisomers synthesized, [trans-(1′R,2′R),6S] isomer 6 exhibited the best BACE1 inhibitory activity, which was statistically superior to that of the corresponding ethylene linker compound (R)-3. Combinational examinations of the binding mode of 6 were performed, which included isothermal titration calorimetry (ITC), X-ray crystallographic structure analysis and theoretical calculations, to clarify the effect of our conformational restriction approach. From the ITC measurement, the binding entropy of 6 was found to be ～0.5 kcal larger than that of (R)-3, which is considered to be affected by conformational restriction with a cyclopropane ring.
The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: Reaction development, scope, and applications
Ebner, David C.,Bagdanoff, Jeffrey T.,Ferreira, Eric M.,McFadden, Ryan M.,Caspi, Daniel D.,Trend, Raissa M.,Stoltz, Brian M.
supporting information; experimental part, p. 12978 - 12992 (2010/06/19)
The first palladium-catalyzed enantioselective oxidation of secondary alcohols has been developed, utilizing the readily available diamine (-)-sparteine as a chiral ligand and molecular oxygen as the stoichiometric oxidant. Mechanistic insights regarding the role of the base and hydrogen-bond donors have resulted in several improvements to the original system. Namely, addition of cesium carbonate and tert-butyl alcohol greatly enhances reaction rates, promoting rapid resolutions. The use of chloroform as solvent allows the use of ambient air as the terminal oxidant at 23°C, resulting in enhanced catalyst selectivity. These improved reaction conditions have permitted the successful kinetic resolution of benzylic, allylic, and cyclopropyl secondary alcohols to high enantiomeric excess with good-toexcellent selectivity factors. This catalyst system has also been applied to the desymmetrization of meso-diols, providing high yields of enantioenriched hydroxyketones.
Stereocontrol with phosphine oxides: Synthesis of optically active cyclopropyl ketones
Nelson, Adam,Warren, Stuart
, p. 3425 - 3433 (2007/10/03)
Treatment of -keto y'-hydroxy phosphine oxides, or silylated hemiacetal derivatives of these compounds, with potassium /e/7-butoxide in /e/7-butyl alcohol leads to the formation of cyclopropyl ketones. The synthesis of optically active 1, 2-di- and 1, 2,
Two-step synthesis of trans-2-arylcyclopropane carboxylates with 98-100% ee by the use of a phosphazene base
Solladie-Cavallo, Ariette,Diep-Vohuule, Ahn,Isarno, Thomas
, p. 1689 - 1691 (2007/10/03)
Only the axial diastereomer of sulfonium salts 2 are formed upon alkylation of 1. Deprotonation of 2 results in ylides, which allow the highly enantioselective cyclopropanation of Michael systems. The chirat auxiliary 1 is recovered and can be reused.
