478488-10-7

Upstream product

• 54125-02-9 danishefsky's diene 
• 104-87-0 4-methyl-benzaldehyde 
• 88146-60-5 1-tert-Butoxy-3-<(trimethylsilyl)oxy>butadiene 
• 71735-01-8 (E)-3-(tert-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene 

Relevant academic research and scientific papers

A highly enantioselective hetero-Diels-Alder reaction of aldehydes with Danishefsky's diene catalyzed by chiral titanium(IV) 5,5′,6,6′,7,7′,8,8′-octahydro-1,1′ -bi-2-naphthol complexes

The catalytic effect of chiral Lewis acids on the hetero-Diels-Alder reaction between aldehydes and Danishefsky's diene (1) has been investigated. A variety of combinations of different ligands and Lewis acids have been examined as catalysts for the heter

Evaluation of catalyst acidity and substrate electronic effects in a hydrogen bond-catalyzed enantioselective reaction

A modular catalyst structure was applied to evaluate the effects of catalyst acidity in a hydrogen bond-catalyzed hetero Diels-Alder reaction. Linear free energy relationships between catalyst acidity and both rate and enantioselectivity were observed, wh

Storable, powdered chiral zirconium complex for asymmetric aldol and hetero Diels-Alder reactions

A storable, powdered chiral zirconium catalyst for asymmetric aldol and hetero Diels-Alder reactions has been developed. The catalyst has the same activity as that prepared in situ even after being stored for 3 months. Moreover, this chiral Zr catalyst wo

Chiral hetero Diels-Alder products by enantioselective and diastereoselective zirconium catalysis. Scope, limitation, mechanism, and application to the concise synthesis of (+)-prelactone C and (+)-9-deoxygoniopypyrone

Catalytic asymmetric hetero Diels-Alder (HDA) reactions using a chiral zirconium complex have been developed. The reactions of aldehydes with Danishefsky's dienes proceeded smoothly to afford the corresponding pyranone derivatives in high yields with high diastereo- and enantioselectivities in the presence of a chiral zirconium complex, which was prepared from zirconium tert-butoxide, (R)-3,3′-diiodobinaphthol or its derivative, a primary alcohol, and a small amount of water. It is noted that 2,3-trans-pyranone derivatives were obtained with remarkably high diastereo- and enantioselectivities in the reaction with 4-methyl Danishefsky's diene. This is the first example of catalytic asymmetric trans-selective hetero Diels-Alder reactions of aldehydes. Furthermore, asymmetric HDA reactions with 4-benzyloxy Danishefsky's dienes were conducted to afford 2,3-cis-pyranone derivatives in high selectivities. Isolation of an intermediate of this asymmetric hetero Diels-Alder reaction indicated that the reaction proceeded in a stepwise cycloaddition pathway. Finally, these catalytic, asymmetric hetero Diels-Alder reactions were successfully applied to concise syntheses of biologically important natural pyranone derivatives, (+)-Prelactone C and (+)-9- deoxygoniopypyrone.

Chiral rare earth organophosphates as homogeneous Lewis acid catalysts for the highly enantioselective hetero-Diels-Alder reactions

Various trivalent rare earth-chiral phosphate complexes [(R)-1-RE, (R)-3-RE, and (R)-4-Ce] were prepared and evaluated as a Lewis acid catalyst for the asymmetric hetero-Diels-Alder reaction of aldehydes with the Danishefsky's diene. Some of them effectiv

Assembled Dendritic Titanium Catalysts for Enantioselective Hetero-Diels-Alder Reaction of Aldehydes with Danishefsky's Diene

A new type of dendritic 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN)-derived Schiff-base ligands have been synthesized and applied to the titanium-catalyzed hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes. These reactions afforded the corresponding 2-substituted 2,3-dihydro-4H-pyran-4-ones in quantitative yields and with excellent enantioselectivities (up to 97.2% ee). The disposition of the dendritic wedges and the dendron size in the ligands were found to have significant impact on the enantioselectivity of the reaction. The recovered dendritic catalyst could be reused without further addition of the Ti source or a carboxylic acid additive for at least three cycles, retaining similar activity and enantioselectivity. The high stability of this type of assembled dendritic titanium catalyst may be attributed to the stabilization effect of large-sized dendron units in the catalyst molecule. The other important phenomenon observed with this catalyst system is that a higher degree of asymmetric amplification has been achieved by attachment of the dendron unit to the chiral ligand, which represents a new advantage of dendrimer catalysts for asymmetric reactions using chiral ligands of lower optical purity.

Catalytic, Asymmetric trans-Selective Hetero Diels-Alder Reactions Using a Chiral Zirconium Complex

matrix presented The first catalytic, asymmetric 2,3-trans-selective hetero Diels-Alder reaction has been developed. The reactions of aldehydes with Danishefsky's dienes proceeded smoothly to afford the pyranone derivatives in high yields with high trans-

Highly efficient enantioselective synthesis of optically active dihydropyrones by chiral titanium (iv) (5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol) complexes

The asymmetric hetero-Diels-Alder reaction of Danishefsky's diene and an aldehyde catalyzed by 20 mol% chiral H8-BINOL-Ti(IV) affords the corresponding 2-substitutent-2,3-dihydro-4H-pyran-4-one with ees of up to 99% under mild reaction conditio

Asymmetric Hetero Diels-Alder Reaction Catalyzed by Chiral Ytterbium(III) Phosphate {Yb[(R)-(-)-BNP]3}: Remarkable Ligand Effect on the Enantioselectivity

2,6-Lutidine was found to be an effective additive for the chiral ytterbium(III) phosphate {Yb[(R)-(-)-BNP]3}-catalyzed asymmetric hetero Diels-Alder reaction thus achieving high enantioselectivity (up to 93% ee) at room temperature.