Highly diastereoselective aldol additions of a chiral ethyl ketone enolate under Lewis base catalysis

Organic Letters

Volumn 3, Issue 14, 2001, Pages 2201-2204

  Denmark, Scott E ^a   Pham, Son M ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

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EID: 0005878554     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0160497     Document Type: Article

References (32)

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9. (a) For a discussion of aldol additions of boron, titanium, and lithium enolates of chiral ethyl ketones, see: Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), Edition E21; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, pp 1612-1622. For related benzyl and benzoate derivatives, see:
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13. Following a modified procedure: Luke, G. P.; Morris, J. J. Org. Chem. 1995, 60, 3013.
14. All compounds have been fully characterized; see the Supporting Information for details.
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21. Denmark, S. E.; Pham, S. M. Unpublished results.
22. In this nomenclature, the first descriptor is relative, the second is internal. The configuration assignment follows degradation to propanoates and chemical correlation as described below.
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26. Following a procedure described by Urpí, ref 6d.
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32. For a discussion of chelation as a stereocontrol element in lactate-derived stannous enolates, see: Paterson, I., Tillyer, R. Tetrahedron Lett. 1992, 33, 4233.