Combinatorial Synthesis of a Small-Molecule Library Based on the Vinyl Sulfone Scaffold

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4437-4440

  Wang, Gang ^a   Yao, Shao Q ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; PROTEINASE INHIBITOR; SULFONE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; HORNER WADSWORTH EMMONS REACTION; MOLECULAR DYNAMICS; MOLECULAR LIBRARY; OXIDATION; SOLID; SYNTHESIS;

EID: 0345359261     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035774+     Document Type: Article

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22. Epimerization of 6 could possibly occur in two ways. One, the chiral center in the starting material, amino aldehyde 5, may be directly epimerized, leading to generation of both isomers in product 6. Alternatively, deconjugation of the vinyl sulfone in product 6 to generate an allylic sulfone, followed by reconjugation, could also lead to direct epimerization of 6. In our studies here, we cannot rule out either possibility.
23. Typical yields were ∼90-95%, with high purity of the desired products (90%) and minimal epimerization (<10%).
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