Direct Catalytic Asymmetric Addition of Alkylnitriles to Aldehydes with Designed Nickel–Carbene Complexes
A direct catalytic asymmetric addition of acetonitrile to aldehydes that realizes over 90 % ee is the ultimate challenge in alkylnitrile addition chemistry. Herein, we report achieving high enantioselectivity by the strategic use of a sterically demanding NiII pincer carbene complex, which afforded highly enantioenriched β-hydroxynitriles. This highly atom-economical process paves the way for exploiting inexpensive acetonitrile as a promising C2 building block in a practical synthetic toolbox for asymmetric catalysis.
Facile construction of functionalized periodic mesoporous organosilica for Ir-catalyzed enantioselective reduction of α-cyanoacetophenones and α-nitroacetophenones
A facile method to construct chiral organoiridium-functionalized periodic mesoporous organosilica is developed. The heterogeneous catalyst displays excellent catalytic efficiency in the enantioselective reduction of α-cyanoacetophenones and α-nitroacetoph
Preparative access to medicinal chemistry related chiral alcohols using carbonyl reductase technology
Libraries of highly enantioenriched secondary alcohols in both enantiomeric forms were synthesised by enzymatic reduction of their parent ketones using selectAZyme carbonyl reductase (CRED) technology. Commercially available CREDs were able to reduce a range of substrate classes efficiently and with very high enantioselectivity. Matching substrate classes to small subsets of CREDs enabled the fast development of preparative bioreductions and the rapid generation of 100-1500 mg samples of chiral alcohols in typically >95% ee and the majority in ≥99.0% ee. The conditions for small scale synthesis were then scaled up to 0.5 kg to deliver one of the chiral alcohols, (S)-1-(4-bromophenyl)-2-chloroethanol, in 99.8% ee and 91% isolated yield.
Rowan, Andrew S.,Moody, Thomas S.,Howard, Roger M.,Underwood, Toby J.,Miskelly, Iain R.,He, Yanan,Wang, Bo
p. 1369 - 1381
(2013/12/04)
Asymmetric reduction of β-ketonitriles with a recombinant carbonyl reductase and enzymatic transformation to optically pure β-hydroxy carboxylic acids
α-Ethylation is concomitant with the reduction of aromatic β-ketonitriles catalyzed by whole-cell biocatalysts. Use of isolated carbonyl reductase has completely eliminated this competing reaction. (R)-β-Hydroxy nitriles were obtained via a reduction cata
Zhu, Dunming,Ankati, Haribabu,Mukherjee, Chandrani,Yang, Van,Biehl, Edward R.,Hua, Ling
p. 2560 - 2563
(2008/02/05)
BIARYL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING THE SAME
The present invention relates generally to the field of anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. More particularly, the invention relates to a family of tricyclic compounds that are useful as such agents.
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Page/Page column 55
(2010/10/20)
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