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- Title
New, Homochiral Synthons Obtained through Simple Manipulations of Enzymatically Derived 3-Halo-cis-1,2-dihydrocatechols.
- Authors
White, Lorenzo V.; Lan, Ping; Schwartz, Brett D.; Willis, Anthony C.; Banwell, Martin G.
- Abstract
The bromoepoxide 5a, which is obtained from the homochiral and enzymatically derived cis-1,2-dihydrocatechol 1a, is readily and efficiently transformed into either isomer 8a or the corresponding methoxymethyl-ether 2a. Though both of these products can be fully characterized, they are somewhat unstable, with the former being converted into the crystalline enone 3a on standing and the latter readily participating in a Diels-Alder cycloaddition reaction with the potent dienophile N-phenyl-1,2,4-triazoline-3,5-dione to give adduct 7a. The single-crystal X-ray structures of compounds 3a and 7a are reported. Using the related chemistry the chloro-analogue, 3b, of enone 3a can be obtained.
- Subjects
ISOMERS; METHOXYMETHYL compounds; CHEMICAL research
- Publication
Australian Journal of Chemistry, 2015, Vol 68, Issue 10, p1467
- ISSN
0004-9425
- Publication type
Article
- DOI
10.1071/CH15061