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Synthesis of D -Desosamine and Analogs by Rapid Assembly of 3-Amino Sugars

D-Desosamine is synthesized in 4 steps from methyl vinyl ketone and sodium nitrite. The key step in this chromatography-free synthesis is the coupling of (R)-4-nitro-2-butanol and glyoxal (trimeric form) mediated by cesium carbonate, which affords in crystalline form 3-nitro-3,4,6-trideoxy-alpha-D-glucose, a nitro sugar stereochemically homologous to D-desosamine. This strategy has enabled the syntheses of an array of analogous 3-nitro sugars. In each case the 3-nitro sugars are obtained in pure form by crystallization.

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Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol

Enantioselective reductive desymmetrization of glutarimides has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process that upgraded the enantioselectivity of an intermediate hydroxy-lactam. The reaction was generally tolerant of a number of substituents in the 4-position, giving enantiomeric excesses of greater than 82%.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Asymmetric synthesis of 3,3-spirooxindoles fused with cyclobutanes through organocatalytic formal [2 + 2] cycloadditions under h-bond-directing dienamine activation

The first organocatalytic asymmetric synthesis of a spirooxindole skeleton incorporated with a cyclobutane moiety has been successfully developed on the basis of H-bond-directing dienamine activation. Structurally complex spirocyclobutyl oxindoles, which possess four contiguous stereocenters, including one spiro quaternary center, were obtained in good yields (up to 83%) with excellent beta,gamma-regioselectivity (>19:1) and stereocontrol (up to >19:1 dr and 97% ee).

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Metal catalyst and ligand design,
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Synthesis and crystal structure of the chiral beta-amino alcohol (S)-alpha,alpha-diphenyl-2-pyrrolidine methanol

Optically pure (S)-alpha,alpha-diphenyl-2-pyrrolidine methanol was prepared from L-proline via protection of the amino group, reaction with the Grignard reagents and deprotection of the amino-protected groups in 54.4% yield. The synthetic conditions to prepare (S)-alpha,alpha-diphenyl-2- pyrrolidinemethanol were optimised. Single crystal X-ray diffraction analysis revealed that the molecular structure of the compound was enantiomerically pure. The crystals are orthorhombic, space group P2(1)2(1)2(1), with unit cell parameters a = 8.9000(18) A, b = 9.2405(18) A, c = 16.671(3) A, V = 1371.1(5) A3, Dx = 1.227 g cm -3, Z =4, T = 113(2)K, F(000) = 628, R1 = 0.0335 and wR2 = 0.0707. The absolute structure parameter was -1.6(17).

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Highly enantioselective borane reduction of prochiral ketones catalyzed by C3-symmetric tripodal beta-hydroxy amides

The asymmetric borane reduction of prochiral ketones with a series of easily constructed chiral C3-symmetric tripodal tris(beta- hydroxyamide) ligands was investigated. The borane complex of chiral ligand 1,1?,?,-(1,3,5-benzenetricarbonyl)-tris[(2S)-alpha, alpha-diphenyl-2-pyrrolidinemethanol] (1h) was found to be an efficient catalyst in asymmetric borane reduction of prochiral ketones and excellent enantioselectivities were obtained with both electron-deficient and electron-rich prochiral ketones (up to 97% ee). Georg Thieme Verlag Stuttgart.

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Synthesis, Structure, and Magnetic Properties of a Mononuclear Chiral (Acetato)bis(aminoalkoxido)manganese(III) Complex

A new synthetic procedure was developed to obtain a novel mononuclear chiral square-pyramidal (acetato)bis(aminoalkoxido)MnIII complex from a heterometallic ZnII/MnII system with a crucial role for O2 in the process. The resulting compound was characterized spectroscopically and crystallographically, and its magnetic properties were determined. The MnIII ion exhibits magnetic anisotropy with a zero-field splitting D parameter equal to ?2.95 cm?1.

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Metal catalyst and ligand design,
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Application of chiral cationic catalysts to several classical syntheses of racemic natural products transforms them into highly enantioselective pathways

This paper describes the application of chiral oxazaborolidinium cations of type 2 to various enantioselective Diels-Alder reactions that have served as early key steps for the syntheses of complex natural products. In the original syntheses these Diels-Alder reactions produced racemic adducts and led to racemic target molecules unless a separation of enantiomers by classical resolution was employed. By use of chiral catalysts of type 2, chiral products were obtained directly from Diels-Alder reactions of achiral components in excellent yield and enantioselectivity and with the mechanistically predicted absolute configuration. As a result, a number of classical syntheses could be converted to enantioselective versions, including (1) cortisone/cortisol (Merck/Sarett), (2) dendrobine (Kende), (3) vitamin B12 (Eschenmoser), (4) myrocin C (Chu-Moyer/Danishefsky), (5) coriolin and hirsutene (Mehta), (6) dendrobatid 251F (Aube), (7) silphinene (Ito), and (8) nicandrenone core (Stoltz/Corey).

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Monomeric organoaluminium complexes RAl(OR*)2 and R2AlOR* with an optically active amino alkoxide ligand

The reactions of trialkylaluminium, R3Al, with (S)-(-)alpha,alpha-diphenyl-2-pyrrolidinyl-methanol have been investigated, in which unusual bis-complexes RAl(OR*)2 were obtained [OR=(S)-alpha,alpha-diphenyl-2-pyrrolidinyl-methoxide (Dpm), R=Me (1), Et (2), 1-Nor (3)]. A similar reaction carried out with R=t-Bu yields, by contrast, the expected mono-alkoxide R2AlOR* (4). All compounds were characterised by X-ray crystallography and NMR spectroscopy. The molecular structures are monomeric. In 1-3, the aluminium centres bonded to the nitrogen atoms of two chelating ligands are five-coordinate, while the metal atom contained in 4 is tetrahedrally surrounded. The absolute structures of all complexes were determined from X-ray diffraction data. The formation of the dative Al-N bonds is stereospecific in all cases.

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Metal catalyst and ligand design,
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Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes

Intramolecular chirality transfer [2 + 2] cycloaddition of enantiomerically enriched allenoates and alkenes is presented. The use of a chiral catalyst was found to be critical to achieve high levels of diastereoselectivity compared to use of an achiral catalyst. The method developed leads to highly substituted cyclobutanes that would be difficult to prepare by alternative methods.

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Direct asymmetric aldol reaction of acetophenones with aromatic aldehydes catalyzed by chiral Al/Zn heterobimetallic compounds

Chiral Al/Zn heterobimetallic complexes are effective catalysts for the direct highly enantioselective aldol reaction of acetophenones with aromatic aldehydes. The Al site in the complex acts as a Lewis acid to activate aldehyde, whereas ethylzinc alkoxide plays a role of a Br¡ãnsted base to form a reactive zinc enolate with acetophenone. Distinct nature of two different metals contributes to the efficient direct asymmetric aldol reaction.

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