Asymmetric hetero-diels-alder reaction of danishefsky's dienes with α-carbonyl esters catalyzed by an indium(III)-PyBox complex
An efficient catalytic enantioselective hetero-Diels-Alder reaction of Danishefsky's dienes with α-carbonyl esters using a chiral In(III)-pybox complex has been demonstrated. This protocol offers several advantages, including mild reaction conditions, relatively low catalyst loading, and good to excellent enantioselectivities. Furthermore, the absolute configurations of the new alkynyl-containing products were determined by CD spectra in combination with TD-DFT calculations.
Zhao, Bei,Loh, Teck-Peng
supporting information
p. 2914 - 2917
(2013/07/26)
Lewis acid catalysis of second-generation metallosalen complexes: An explanation for stereochemistry of asymmetric hetero Diels-Alder reaction
Chloro nitrosyl (R,S)-(salen)ruthenium(II) complex served as a good catalyst for asymmetric hetero Diels-Alder (HDA) reaction of Danishefsky's diene with a wide variety of aldehydes. In contrast with this, (R,R)-(salen)-chromium(III) and -manganese(III) c
Asymmetric hetero Diels-Alder reaction of Danishefsky's dienes and glyoxylates with chiral bis(oxazolinyl)phenylrhodium(III) aqua complexes, and its mechanistic studies
Asymmetric hetero Diels-Alder reaction of Danishefsky's dienes with glyoxylates is catalyzed in high enantioselectivity and cis (endo)-diastereoselectivity by chiral (Phebox)RhCl2(H2O) complexes [Phebox=2,6-bis(oxazolinyl)phenyl], via the concerted [4+2] mechanism with perpendicular conformation of two carbonyl moieties of glyoxylates. Dibromide and difluoride complexes were newly synthesized and found to exhibit a slightly higher enantioselectivity of the hetero Diels-Alder products than the parent dichloride complex (Cl: 80% ee, Br: 82% ee, F: 84% ee).
Asymmetric hetero-Diels-Alder reaction of glyoxylate esters and Danishefsky's diene catalyzed by chiral bis(oxazoline)-lanthanide complexes
Asymmetric hetero-Diels-Alder reactions of glyoxylate esters and Danishefsky's diene catalyzed by various chiral bis(oxazoline)-lanthanide complexes afforded the corresponding aldol adducts, which upon treatment with trifluoroacetic acid, furnished the he
Qian, Changtao,Wang, Longcheng
p. 2203 - 2206
(2007/10/03)
Asymmetric hetero Diels-Alder reactions of Danishefsky's diene and glyoxylate esters catalyzed by chiral bisoxazoline derived catalysts
Asymmetric hetero Diels-Alder reactions of Danishefsky's diene and glyoxylate esters catalyzed by bis(oxazoline)-metal complex afforded the corresponding aldol adduct which upon treatment with trifluoroacetic acid furnished the hetero Diels-Alder product in 72% enantiomeric excess and 70% isolated yield.
Asymmetric Catalysis of Diels-Alder Cycloaddition by a β-Amino Alcohol Derived Boron Complex: Reasonable Transition-state Assembly for One-directional Diene Approach
Asymmetric Diels-Alder reactions of glyoxylate with acid-labile Danishefsky dienes are catalysed in high enantio- and cis(endo)-diastereo-selectivity by a chiral amino alcohol derived boron complex, via the favourable transition-state assembly for one-directional diene-approach from the site proximal to the sulfonylamino moiety.
Motoyama, Yukihiro,Mikami, Koichi
p. 1563 - 1564
(2007/10/02)
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