Asymmetric addition reactions of Grignard reagents to chiral 2-trifluoromethyl tert-butyl (Ellman) sulfinimine-ethanol adducts

Tetrahedron Letters

Volumn 47, Issue 14, 2006, Pages 2377-2381

  Kuduk, Scott D ^a   Marco, Christina Ng Di ^a   Pitzenberger, Steven M ^a   Tsou, Nancy ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33644784912     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.154     Document Type: Article

References (24)

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13. 2 (M+Na): 270.0746. Found: 270.0746.
14. Perspective view (ORTEP) of 6b showing crystallographic numbering scheme. Non-hydrogen atoms are represented by ellipsoids corresponding to 50% probability envelopes. Hydrogen atoms have been drawn at an arbitrary size.
15. +).
16. The addition of vinyl Grignard to a chiral trifluoroacetaldehyde hydrazone has been reported: see, S. Fries, J. Pytkowiz, and T. Brigaud Tetrahedron Lett. 46 2005 4761 4764
17. Alternatively, the direct trifluoromethylation of α,β-unsaturated N-tert-butyl sulfinimes has been reported: see: G.K. Surya Prakash, M. Mandal, and G.A. Olah Org. Lett. 3 2001 2847 2850
18. Only one geometric isomer of 2 was observed.
19. S,S). Perspective view (ORTEP) of 11, showing crystallographic numbering scheme. Non-hydrogen atoms are represented by ellipsoids corresponding to 50% probability envelopes. Hydrogen atoms have been drawn at an arbitrary size. CCDC 296065 (6b ) and 296066 (11 ) contain the supplementary crystallographic data for this letter. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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22. While the synthesis of related α-trifluoromethyl nitrogen heterocycles has been reported by the RCM approach, this represents the first example in which a five membered ring is formed: see: S. Gille, A. Ferry, T. Billard, and B. Langlois J. Org. Chem. 68 2003 8932 8935
23. S,S) by comparison with literature data: see: G.K. Surya Prakash, M. Mandal, and G.A. Olah Angew. Chem., Int. Ed. 40 2001 589 590
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