http://repository.iitr.ac.in/handle/123456789/3061| Title: | Zn-ProPhenol Catalyzed Enantio- and Diastereoselective Direct Vinylogous Mannich Reactions between ?,?- and ?,y-Butenolides and Aldimines |
| Authors: | Trost B.M. Gnanamani, Elumalai Tracy J.S. Kalnmals C.A. |
| Published in: | Journal of the American Chemical Society |
| 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 ?,?- and ?,y-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 required 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. © 2017 American Chemical Society. |
| Citation: | Journal of the American Chemical Society (2017), 139(50): 18198-18201 |
| URI: | https://doi.org/10.1021/jacs.7b11361 http://repository.iitr.ac.in/handle/123456789/3061 |
| Issue Date: | 2017 |
| Publisher: | American Chemical Society |
| ISSN: | 27863 |
| Author Scopus IDs: | 57217139833 35319775800 56818624200 56716397100 |
| Author Affiliations: | Trost, B.M., Department of Chemistry, Stanford University, Stanford, CA 94305, United States Gnanamani, E., Department of Chemistry, Stanford University, Stanford, CA 94305, United States Tracy, J.S., Department of Chemistry, Stanford University, Stanford, CA 94305, United States Kalnmals, C.A., Department of Chemistry, Stanford University, Stanford, CA 94305, United States |
| Funding Details: | We thank the NSF (CHE-1360634) and the NIH (GM-033049) for financial support of our programs. We also acknowledge Prof. Allen Oliver (University of Notre Dame) for X-ray crystallographic analysis. |
| Corresponding Author: | Trost, B.M.; Department of Chemistry, Stanford UniversityUnited States; email: bmtrost@stanford.edu |
| Appears in Collections: | Journal Publications [CY] |
Items in Repository are protected by copyright, with all rights reserved, unless otherwise indicated.