Highly enantioselective organocatalysis of the Hajos-Parrish-Eder-Sauer- Wiechert reaction by the β-amino acid cispentacin

Chemical Communications

Volumn , Issue 30, 2005, Pages 3802-3804

  Davies, Stephen G ^a   Sheppard, Ruth L ^a   Smith, Andrew D ^a   Thomson, James E ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOCYCLOPENTANECARBOXYLIC ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HAJOS PARRISH EDER SAUER WIECHERT REACTION;

EID: 23744502728     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b506780b     Document Type: Article

References (34)

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26. The cyclisation of 1 to 2 is slower with (1R,25)-cispentacin than L-proline; for example 30 mol% L-proline promotes the cyclisation of triketone 1 to 2 in 24 hours; 70% conversion to 2 is seen with 30 mol% of (1R,2S)-cispentacin after 24 hours. In MeCN, no reaction was observed using (1R,25)-cispentacin for the cyclisation of 1 to 2; (1R,2S)-N-methyl-cispentacin was inactive as a catalyst in this reaction manifold.
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