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Please use this identifier to cite or link to this item: 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]

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