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Title: Synthesis of a Chiral Auxiliary Family from Levoglucosenone and Evaluation in the Diels–Alder Reaction
Contributor(s): Klepp, Julian  (author); Sumby, Christopher J (author); Greatrex, Ben W  (author)orcid 
Publication Date: 2018
Early Online Version: 2018-05-25
DOI: 10.1055/s-0037-1610148
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Abstract: A new family of chiral auxiliaries has been developed based on the lignocellulosic biomass pyrolysis product levoglucosenone. A promising single stereoisomer with an alcohol and π-stacking phenyl substituents was prepared in excellent yield in two steps from di­hydrolevoglucosenone without chromatography on >50 g scale. Acrylate esters prepared from the auxiliaries underwent diastereoselective Lewis acid promoted Diels–Alder reactions with cyclopentadiene (­endo/exo 98:2, endo d.r. up to 98:2), dimethylbutadiene (d.r. 93:7), and isoprene (d.r. > 98:2)
Publication Type: Journal Article
Source of Publication: Synlett, 29(11), p. 1441-1446
Publisher: Georg Thieme Verlag
Place of Publication: Germany
ISSN: 0936-5214
Field of Research (FoR) 2008: 030503 Organic Chemical Synthesis
030504 Organic Green Chemistry
Socio-Economic Objective (SEO) 2008: 970103 Expanding Knowledge in the Chemical Sciences
860604 Organic Industrial Chemicals (excl. Resins, Rubber and Plastics)
860899 Human Pharmaceutical Products not elsewhere classified
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
Appears in Collections:Journal Article
School of Rural Medicine
School of Science and Technology

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