Asymmetric enolate alkylation via templation with chiral synthetic receptors

Tetrahedron Letters

Volumn 45, Issue 3, 2004, Pages 501-504

  Postnikova, Brenda J ^a   Anslyn, Eric V ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Enolate alkylation; Molecular recognition

Indexed keywords

2 ACETYLCYCLOHEXANONE; ALKANONE; CARBENE; ENOLASE; RECOMBINANT RECEPTOR; SODIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; BENZYLATION; CHIRALITY; ENANTIOSELECTIVITY; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; TITRIMETRY;

EID: 0346993612     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.002     Document Type: Article

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17. 4. After filtration, the filtrate was concentrated in vacuo to give a yellow oil. This crude product was purified by flash chromatography (hexanes/ethyl acetate (90/10)) to give the desired product.
18. (a) For other enantioselective tripodal directed reactions see: Kim S.-G., Ahn K.H. Tetrahedron Lett. 42:2001;4175-4177 (b) Kim S.-G., Kim K.-H., Jung J., Shin S.K., Ahn K.H. J. Am. Chem. Soc. 124:2002;591-596 (c) Kim S.-G., Ahn K.H. Chem. Eur. J. 6:2000;3399-3403 (d) Pascal R.A. Jr., Mathai M.S., Shen X., Ho D.M. Angew. Chem., Int. Ed. 40:2001;4046-4048 (e) Kim H.-J., Kim Y.-H., Hong J.-I. Tetrahedron Lett. 42:2001;5049-5052 (f) . For a review see: Moberg C. Angew. Chem., Int. Ed. 37:1998;248-268.
19. (a) For other enantioselective tripodal directed reactions see: Kim S.-G., Ahn K.H. Tetrahedron Lett. 42:2001;4175-4177 (b) Kim S.-G., Kim K.-H., Jung J., Shin S.K., Ahn K.H. J. Am. Chem. Soc. 124:2002;591-596 (c) Kim S.-G., Ahn K.H. Chem. Eur. J. 6:2000;3399-3403 (d) Pascal R.A. Jr., Mathai M.S., Shen X., Ho D.M. Angew. Chem., Int. Ed. 40:2001;4046-4048 (e) Kim H.-J., Kim Y.-H., Hong J.-I. Tetrahedron Lett. 42:2001;5049-5052 (f) . For a review see: Moberg C. Angew. Chem., Int. Ed. 37:1998;248-268.
20. (a) For other enantioselective tripodal directed reactions see: Kim S.-G., Ahn K.H. Tetrahedron Lett. 42:2001;4175-4177 (b) Kim S.-G., Kim K.-H., Jung J., Shin S.K., Ahn K.H. J. Am. Chem. Soc. 124:2002;591-596 (c) Kim S.-G., Ahn K.H. Chem. Eur. J. 6:2000;3399-3403 (d) Pascal R.A. Jr., Mathai M.S., Shen X., Ho D.M. Angew. Chem., Int. Ed. 40:2001;4046-4048 (e) Kim H.-J., Kim Y.-H., Hong J.-I. Tetrahedron Lett. 42:2001;5049-5052 (f) . For a review see: Moberg C. Angew. Chem., Int. Ed. 37:1998;248-268.
21. (a) For other enantioselective tripodal directed reactions see: Kim S.-G., Ahn K.H. Tetrahedron Lett. 42:2001;4175-4177 (b) Kim S.-G., Kim K.-H., Jung J., Shin S.K., Ahn K.H. J. Am. Chem. Soc. 124:2002;591-596 (c) Kim S.-G., Ahn K.H. Chem. Eur. J. 6:2000;3399-3403 (d) Pascal R.A. Jr., Mathai M.S., Shen X., Ho D.M. Angew. Chem., Int. Ed. 40:2001;4046-4048 (e) Kim H.-J., Kim Y.-H., Hong J.-I. Tetrahedron Lett. 42:2001;5049-5052 (f) . For a review see: Moberg C. Angew. Chem., Int. Ed. 37:1998;248-268.
22. (a) For other enantioselective tripodal directed reactions see: Kim S.-G., Ahn K.H. Tetrahedron Lett. 42:2001;4175-4177 (b) Kim S.-G., Kim K.-H., Jung J., Shin S.K., Ahn K.H. J. Am. Chem. Soc. 124:2002;591-596 (c) Kim S.-G., Ahn K.H. Chem. Eur. J. 6:2000;3399-3403 (d) Pascal R.A. Jr., Mathai M.S., Shen X., Ho D.M. Angew. Chem., Int. Ed. 40:2001;4046-4048 (e) Kim H.-J., Kim Y.-H., Hong J.-I. Tetrahedron Lett. 42:2001;5049-5052 (f) . For a review see: Moberg C. Angew. Chem., Int. Ed. 37:1998;248-268.
23. (a) For other enantioselective tripodal directed reactions see: Kim S.-G., Ahn K.H. Tetrahedron Lett. 42:2001;4175-4177 (b) Kim S.-G., Kim K.-H., Jung J., Shin S.K., Ahn K.H. J. Am. Chem. Soc. 124:2002;591-596 (c) Kim S.-G., Ahn K.H. Chem. Eur. J. 6:2000;3399-3403 (d) Pascal R.A. Jr., Mathai M.S., Shen X., Ho D.M. Angew. Chem., Int. Ed. 40:2001;4046-4048 (e) Kim H.-J., Kim Y.-H., Hong J.-I. Tetrahedron Lett. 42:2001;5049-5052 (f) . For a review see: Moberg C. Angew. Chem., Int. Ed. 37:1998;248-268.