190835-53-1

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 54125-02-9 danishefsky's diene 
• 1896-62-4 (E)-benzalacetone 
• 389796-43-4 Acetic acid (2S,6S)-6-isopropoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester 
• 389796-42-3 (2S,6S)-2-Chloromethyl-6-isopropoxy-3,6-dihydro-2H-pyran 
• 154026-92-3 Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate 
• 331686-77-2 ((2S,6S)-6-Isopropoxy-3,6-dihydro-2H-pyran-2-yl)-methanol 
• 331686-78-3 (2S,6S)-6-Isopropoxy-3,6-dihydro-2H-pyran-2-carbaldehyde 
• 135999-61-0 (S)-6-chloromethyl-5,6-dihydropyran-2-one 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

A novel chiral H′4-NOBIN schiff base for hetero-diels-alder reaction of danishefsky's diene with aldehydes

Novel chiral H′4-NOBIN was synthesized in 66% yield through partial hydrogenation of 2-amino-2′-hydroxy-1,1′-binaphthyl, and the structure was proved via X-ray analysis of its salicylaldehyde Schiff base, which was tested in the enantioselectiv

Highly enantioselective hetero-Diels-Alder reactions between Rawal's diene and aldehydes catalyzed by chiral dirhodium(ii) carboxamidates

The first example of a chiral Lewis acid-catalyzed enantioselective hetero-Diels-Alder (HDA) reaction between 1-dimethylamino-3-silyloxy-1,3- butadiene (Rawal's diene) and aldehydes is described. The cycloaddition reaction under the influence of 1 mol% of

BINOlate-magnesium catalysts for enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes

An efficient catalytic enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes using the magnesium binaphthoxide system has been developed, affording a variety of 2-substituted 2,3-dihydro-4H-pyran-4-ones in high yields and with

Asymmetric hetero Diels-Alder reaction catalyzed by chromium complexes of heterogeneously hybridized salen/salan ligands

Various heterogeneously or homogeneously hybridized salen/salan ligands were synthesized, and study of hetero Diels-Alder reactions using their chromium complexes as catalysts revealed that a well-designed heterogeneously hybridized ligand serves as a chi

Chromium-thiophene-salen-based polymers for heterogeneous asymmetric hetero-Diels-Alder reactions

New chiral thiophene-salen ligands have been synthesized and the corresponding chromium complexes proved to be efficient catalysts for promoting asymmetric hetero-Diels-Alder reactions with good activities and high enantio-selectivities (up to 88% ee). Th

Chiral chromium(III) porphyrins as highly enantioselective catalysts for Hetero-Diels-Alder reactions between aldehydes and dienes

Starting from enantiomerically pure 5,10,15,20-tetrakis[(1S,4R,5R,8S)-1,2, 3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-yl]porphyrin, treatment with CrCl2 and subsequent air oxidation afforded the corresponding Cr(III) complex, with chlo

DIANANE-CrIII-salen complexes as highly enantioselective catalysts for hetero-Diels-Alder reactions of aldehydes with dienes

A new type of chromium-salen complex bearing DIANANE (endo,endo-2,5- diaminonorbornane) as chiral backbone has been synthesized and applied to the hetero-Diels-Alder reaction of Danishefsky's diene with various aldehydes. The reactions afford the correspo

A new dirhodium(II) carboxamidate complex as a chiral Lewis acid catalyst for enantioselective hetero-Diels-Alder reactions

Excellent enantioselectivities (up to 99% ee) and turnover numbers (up to 48000) were attained in the hetero-Diels-Alder reaction of a diverse range of aldehydes and activated dienes catalyzed by [Rh2(S-bptpi) 4] (see scheme).

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