Selectivity in the Addition Reactions of Organometallic Reagents to Aziridine-2-carboxaldehydes The Effects of Protecting Groups and Substitution Patterns文档.pdfVIP

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Selectivity in the Addition Reactions of Organometallic Reagents to Aziridine-2-carboxaldehydes The Effects of Protecting Groups and Substitution Patterns文档.pdf

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Selectivity in the Addition Reactions of Organometallic Reagents to Aziridine-2-carboxaldehydes The Effects of Protecting Groups and Substitution Patterns文档

NIH Public Access Author Manuscript Chemistry. Author manuscript; available in PMC 2015 January 21. N Published in final edited form as: I H Chemistry. 2011 October 24; 17(44): 12326–12339. doi:10.1002/chem.201101168. - P A A u Selectivity in the Addition Reactions of Organometallic Reagents t h o r to Aziridine-2-carboxaldehydes: The Effects of Protecting M a Groups and Substitution Patterns n u s c a b a a Aman Kulshrestha , Jennifer M. Schomaker , Daniel Holmes , Richard J. Staples , James r i p E. Jackson*,a, and Babak Borhan*,a t aDepartment of Chemistry, Michigan State University East Lansing, MI 48824 (USA) bDepartment of Chemistry, University of Wisconsin 1101 University Avenue, Madison, WI 53706 (USA) N Abstract I H Good to excellent stereo-selectivity has been found in the addition reactions of Grignard and - P A organo-zinc reagents to N-protected aziridine-2-carboxaldehydes. Specifically, high syn A selectivity was obtained with benzyl-protected cis, tert-butyloxycar-bonyl-protected trans, and u t h tosyl-pro-tected 2,3-disubstituted aziridine-2-car-boxaldehydes. Furthermore, rate and selectivity o r effects of ring substituents, temperature, solvent, and Lewis acid and base modifiers were studied. M The diastereomeric preference of addition is dominated by the substrate aziri-dines’ substitution a n pattern and especially the electronic character and conformational preferences of the