Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 11, Pages 2598-2601Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201800020
Keywords
aldol reactions; asymmetric catalysis; cooperative catalysis; formal synthesis; thioamide
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Funding
- ACT-C from JST [JPMJCR12YO]
- KAKENHI from JSPS [17H03025, 17K08384, JP16H01043]
- MEXT
- Grants-in-Aid for Scientific Research [16H01043, 17K08384, 17H03025, 15F15412] Funding Source: KAKEN
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The direct catalytic asymmetric aldol reaction is an emerging catalytic methodology that provides atom-economical access to functionalized chiral building blocks. Thioamides are useful aldol donors due to their high-fidelity chemoselective enolization and divergent post-aldol transformations. Herein we describe the incorporation of an -vinyl appendage on a thioamide, which expands the utility of aldol adducts for natural product synthesis. This vinylated thioamide was not accommodated under the previously identified catalyst settings, but the newly developed catalytic conditions furnished aldol products containing the pendant vinyl group.
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