340161-66-2Relevant academic research and scientific papers
A general and highly selective chelate-controlled intermolecular oxidative heck reaction
Delcamp, Jared H.,Brucks, Alexandria P.,White, M. Christina
supporting information; scheme or table, p. 11270 - 11271 (2009/02/05)
A novel chelate-controlled intermolecular oxidative Heck reaction is reported that proceeds with a wide range of nonresonance stabilized α-olefin substrates and organoboron reagents to afford internal olefin products in good yields and outstanding regio- and E:Z stereoselectivities. Pd-H isomerization, common in many Heck reactions, is not observed under these mild, oxidative conditions. This is evidenced by outstanding E:Z selectivities (>20:1 in all cases examined), no erosion in optical purity for proximal stereogenic centers, and a tolerance for unprotected alcohols. Remarkably, a single metal/ligand combination, Pd/bis-sulfoxide complex 1, catalyzes this reaction over a broad range of coupling partners. Given the high selectivities and broad scope, we anticipate this intermolecular Heck reaction will find heightened use in complex molecule synthesis. Copyright
Stereoselective synthesis of highly enantioenriched 3-methyl-2-cyclohexen-1-ones possessing an asymmetric quaternary carbon as C-4 or C-6: a sugar template approach
Kubo, Hiroto,Kozawa, Ikuko,Takao, Ken-ichi,Tadano, Kin-ichi
, p. 1203 - 1207 (2008/09/17)
The 1,4-addition of the enolate generated from α-methylated acetoacetate incorporated at C-4 of methyl 6-deoxy-2,3-di-O-(tert-butyldimethylsilyl)-α-d-glucopyranoside to methyl vinyl ketone, followed by aldol condensation of the resulting 1,4-addition prod
MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-kB ACTIVITY AND USE THEREOF
-
Page/Page column 63, (2010/11/25)
Non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-?B activity including obesity, diabetes, inflammatory and immune diseases, and have the structure of formula (I) or an enantiomer, a diastereomer, a pharmaceutically acceptable salt, or hydrate thereof, where J is selected from NR1 or C(R4)(R4a); K is selected from NR2 or C(R5)(R5a); L is selected from NR3 or C(R6)(R6a); and A, X, Y, R1, R2, R3, R4, R4a, R5, R5a, R6, R6a, R8, R10, R11, and n are defined herein. Also provided are pharmaceutical compositions and methods of treating obesity, diabetes and inflammatory or immune associated diseases comprising said compounds.
New auxiliaries for copper-catalyzed asymmetric Michael reactions: Generation of quaternary stereocenters at room temperature
Christoffers, Jens,Mann, Alexander
, p. 1014 - 1027 (2007/10/03)
Dialkyl amides of L-valine, L-isoleucine, and L-tert-leucine (2) are excellent chiral auxiliaries for the construction of quaternary stereocenters at ambient temperature. Enaminoesters 3, prepared from these auxiliaries 2 and Michael donors 1. undergo a copper-catalyzed asymmetric Michael reaction with methyl vinyl ketone (MVK, 4) to afford products 5 in 70-90% yield and 90-99% ee (enantiomeric excess). The exclusion of moisture or oxygen is not necessary. The auxiliaries 2 are readily available by standard procedures. After workup they can be recovered almost quantitatively.
Easy access to optically active Hagemann's esters
Nour, Mohammed,Tan, Kimny,Jankowski, Raphael,Cave, Christian
, p. 765 - 769 (2007/10/03)
The synthesis of optically active Hagemann's esters was investigated. The starting materials in this approach were enamino esters (R,Z)-8, prepared through the condensation of keto ester 6 with (R)-1-phenylethylamine 7. Michael addition reaction of the en
THE STEREOSELECTIVE α-ALKYLATION OF CHIRAL β-HYDROXY ESTERS AND SOME APPLICATIONS THEREOF
Frater, G.,Mueller, U.,Guenther, W.
, p. 1269 - 1278 (2007/10/02)
The stereoselectivity of the α-alkylation of chiral β-hydroxy ester is discussed.The configuration of the alkylated product was proved chemically (Scheme 2) .A one pot aldol-alkylation reaction was developed leading stereoselectively to racemic(S*,S*)-α-alkyl-β-hydroxy ester (Scheme 3,4) .Baker's yeast reduction of 2-alkyl-3-keto ester led to valuable chiral (2RS,3S)-intermediates, which were converted via the corresponding dianion to compounds with a chiral quaternary C atom (Scheme 6) .Synthetic applications of the above findings are shown in the synthesis of various chiral compounds (Scheme 8 and 9) .
