Enantioselective partial reduction of 2,5-disubstituted pyrroles via a chiral protonation approach

Organic Letters

Volumn 6, Issue 18, 2004, Pages 3055-3058

  Donohoe, Timothy J ^a   Freestone, Graeme C ^a   Headley, Catherine E ^a   Rigby, Caroline L ^a   Cousins, Rick P C ^b   Bhalay, Gurdip ^c  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c NOVARTIS HORSHAM RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EPHEDRINE; PYRROLE DERIVATIVE; PYRROLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CRYSTALLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; PROTON TRANSPORT; REACTION ANALYSIS; REDUCTION; SUBSTITUTION REACTION; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; EPHEDRINE; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRROLES; STEREOISOMERISM;

EID: 4544248644     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049014q     Document Type: Article

References (16)

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15. 4Cl quench made no difference to the outcome of this reaction. This control was performed to check if anion B was formed with high enantioselectivity and then racemizing; the results showed that it was not.
16. We thank a referee for useful comments about our model and for the suggestion that cis- and trans-2 might interconvert after the addition of ephedrine to dianion A. In a control experiment, exposure of cis-2 to the lithium alkoxide of ephedrine at -78°C showed that it was inert to deprotonation.