Journal article
Zn-ProPhenol Catalyzed Enantio- and Diastereoselective Direct Vinylogous Mannich Reactions between alpha,beta- and beta,gamma-Butenolides and Aldimines
Journal of the American Chemical Society, Vol.139(50), pp.18198-18201
12/20/2017
PMID: 29198100
Web of Science ID: WOS:000418783600017
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Abstract
We report a Zn-ProPhenol catalyzed reaction between butenolides and imines to obtain tetrasubstituted vinylogous Mannich products in good yield and diastereoselectivity with excellent enantioselectivity (97 to >99.5% ee). Notably, both alpha,beta- and beta,gamma-butenolides can be utilized as nucleophiles in this transformation. The imine partner bears the synthetically versatile N-Cbz group, avoiding the use of the specialized aryl directing groups previously requited in related work. Additionally, the reaction can be performed on gram scale with reduced catalyst loading as low as 2 mol %. The functional group-rich products can be further elaborated using a variety of methods.
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Details
- Title
- Zn-ProPhenol Catalyzed Enantio- and Diastereoselective Direct Vinylogous Mannich Reactions between alpha,beta- and beta,gamma-Butenolides and Aldimines
- Publication Details
- Journal of the American Chemical Society, Vol.139(50), pp.18198-18201
- Resource Type
- Journal article
- Publisher
- American Chemical Society
- Number of pages
- 4
- Grant note
- GM-033049 / NIH; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA CHE-1360634 / NSF; National Science Foundation (NSF)
- Copyright
- © 2017 American Chemical Society
- Identifiers
- WOS:000418783600017; 99381709285806600
- Academic Unit
- Chemistry; Hal Marcus College of Science and Engineering
- Language
- English