Planar chiral PHANOLS as organocatalysts for the Diels-Alder reaction via double hydrogen-bonding to a carbonyl group

Synlett

Volumn , Issue 8, 2003, Pages 1121-1124

  Braddock, D Christopher ^a   MacGilp, Iain D ^b   Perry, Benjamin G ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Carbonyl activation; Diels Alder reactions; Double hydrogen bonding; Organocatalysis; Planar chiral bisphenols

Indexed keywords

4,12 DIBROMO 7,15 DINITRO[2.2]PARACYCLOPHANE; 4,12 DIHYDROXY 7,15 DINITRO[2.2]PARACYCLOPHANE; 4,12 DIHYDROXY[2.2]PARACYCLOPHANE; 4,12 DIMETHOXY 7,15 DINITRO[2.2]PARACYCLOPHANE; 4,4' ISOPROPYLIDENEDIPHENOL; ALDEHYDE; CARBONYL DERIVATIVE; CYCLOPHANE DERIVATIVE; KETONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHIRALITY; DIELS ALDER REACTION; HYDROGEN BOND; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0038729625     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39890     Document Type: Article

References (25)

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25. 2, with a 10-fold excess of diene at 55°C, whereas for PHANOL (10 mol%) a 1:1 stoichiometry of diene:dienophile was employed with no solvent at ambient temperature: the conditions are not directly comparable. However, for the two entries that were run at ambient temperature in Kelly's work (1. 10 equiv CpH, 1 equiv MVK, 40 mol% catalyst, 10 min, 90% conversion; 2. 10 equiv CpH, 1 equiv acrolein, 40 mol% catalyst, 30 min, 76%), comparable conversions were obtained using just 10 mol% PHANOL (Table 1, entries 2, 7).