Use of alkyl 2,4,6-triisopropylbenzoates in the asymmetric homologation of challenging boronic esters

Chemical Communications

Volumn 47, Issue 47, 2011, Pages 12592-12594

  Larouche Gauthier, Robin ^a   Fletcher, Catherine J ^a   Couto, Irantzu ^a   Aggarwal, Varinder K ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2,4,6 TRIISOPROPYLBENZOATE; ALKYL GROUP; BENZOIC ACID DERIVATIVE; BORONIC ACID DERIVATIVE; CARBAMIC ACID DERIVATIVE; ESTER DERIVATIVE; SPARTEINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; COMPARATIVE STUDY; CONTROLLED STUDY; LITHIATION;

EID: 80055005815     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c1cc14469c     Document Type: Article

References (32)

1. D. S. Matteson D. Majumder J. Am. Chem. Soc. 1980 102 7588
2. D. S. Matteson D. Ray J. Am. Chem. Soc. 1980 102 7590
3. D. S. Matteson Tetrahedron 1989 45 1859
4. D. S. Matteson Tetrahedron 1998 54 10555
5. V. K. Aggarwal G. Y. Fang A. T. Schmidt J. Am. Chem. Soc. 2005 127 1642
6. G. Y. Fang V. K. Aggarwal Angew. Chem., Int. Ed. 2007 46 359
7. D. Howells R. Robiette G. Y. Fang L. S. Knowles M. D. Woodrow J. N. Harvey V. K. Aggarwal Org. Biomol. Chem. 2008 6 1185
8. P. R. Blakemore M. S. Burge J. Am. Chem. Soc. 2007 129 3068
9. P. R. Blakemore S. P. Marsden H. D. Vater Org. Lett. 2006 8 773
10. C. R. Emerson L. N. Zakharov P. R. Blakemore Org. Lett. 2011 13 1318
11. D. Hoppe F. Hintze P. Tebben Angew. Chem., Int. Ed. Engl. 1990 29 1422
12. D. Hoppe F. Hintze Angew. Chem., Int. Ed. Engl. 1997 36 2282
13. A. Basu S. Thayumanavan Angew. Chem., Int. Ed. 2002 41 716
14. D. Hoppe, F. Marr and M. Brüggemann, Organolithiums in Enantioselective Synthesis, ed., D. M. Hodgson, Springer, Heidelberg, 2003, pp. 61-137
15. J. L. Stymiest G. Dutheuil A. Mahmood V. K. Aggarwal Angew. Chem., Int. Ed. 2007 46 7491
16. G. Dutheuil M. P. Webster P. A. Worthington V. K. Aggarwal Angew. Chem., Int. Ed. 2009 48 6317
17. M. P. Webster B. M. Partridge V. K. Aggarwal Org. Synth. 2011 88 247
18. G. Besong K. Jarowicki P. J. Kocienski E. Sliwinski F. T. Boyle Org. Biomol. Chem. 2006 4 2193
19. M. J. Dearden C. R. Firkin J.-P. R. Hermet P. O'Brien J. Am. Chem. Soc. 2002 124 11870
20. A. J. Dixon M. J. McGrath P. O'Brien Org. Synth. 2006 83 141
21. P. Beak B. G. McKinnie J. Am. Chem. Soc. 1977 99 5213
22. P. Beak M. Baillargeon L. G. Carter J. Org. Chem. 1978 43 4255
23. P. Beak L. G. Carter J. Org. Chem. 1981 46 2363
24. D. C. Kapeller F. Hammerschmidt J. Org. Chem. 2009 74 2380
25. P. Beak L. G. Carter J. Org. Chem. 1981 46 2363
26. V. K. Aggarwal G. Y. Fang X. Ginesta D. M. Howells M. Zaj Pure Appl. Chem. 2006 78 215
27. A. Bottoni M. Lombardo A. Neri C. Trombini J. Org. Chem. 2003 68 3397
28. R. Robiette G. Y. Fang J. N. Harvey V. K. Aggarwal Chem. Commun. 2006 741
29. Homoallylic 2,4,6-triisopropylbenzoates have been employed in the preparation of chiral allylboronic esters which were ultimately used in a stereocontrolled synthesis of solandelactone: F. A. Robinson and V. K. Aggarwal, manuscript in preparation
30. Boronic Acids-Preparation, Applications in Organic Synthesis and Medicine, ed., D. G. Hall, Wiley-VCH, Weinheim, 2005
31. C. M. Crudden B. W. Glasspoole C. J. Lat Chem. Commun. 2009 6704
32. R. Larouche-Gauthier, T. G. Elford and V. K. Aggarwal, manuscript in preparation