Controlling enantioselectivity in additions to cyclic oxocarbenium ions via transition-metal catalysis

Synlett

Volumn 23, Issue 12, 2012, Pages 1705-1708

  Watson, Mary P ^a   Maity, Prantik ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

alkyne addition; asymmetric catalysis; enantioselectivity; oxocarbenium ions; transition metals

Indexed keywords

CARBON; COPPER; ELECTROPHILE; NUCLEOPHILE; ORGANOMETALLIC COMPOUND; OXOCARBENIUM ION; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ALKYNYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; ENANTIOSELECTIVITY; PROCESS CONTROL;

EID: 84863098536     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290697     Document Type: Article

References (39)

1. Carreira EM, Kvaerno L. Classics in Stereoselective Synthesis. Wiley-VCH Weinheim: 2009
2. Ishihara K, Yamamoto H. Chiral Bronsted/Lewis Acid Catalysis In New Frontiers in Asymmetric Catalysis. Mikami K, Lautens M. John Wiley & Sons Hoboken: 2007; 359 381
3. Kobayashi S, Ishitani H. Chem. Rev.: 1999; 99 1069
4. Braun M, Kotter W. Angew. Chem. Int. Ed.: 2004; 43 514
5. Reisman SE, Doyle AG, Jacobsen EN. J. Am. Chem. Soc.: 2008; 130 7198
6. Moquist PN, Kodama T, Schaus SE. Angew. Chem. Int. Ed.: 2010; 49 7096
7. Umebayashi N, Hamashima Y, Hashizume D, Sodeoka M. Angew. Chem. Int. Ed.: 2008; 47 4196
8. Sodeoka M, Hamashima Y. Chem. Commun.: 2009; 5787
9. Maity P, Srinivas H, Watson M. J. Am. Chem. Soc.: 2011; 133 17142
10. Kobayashi S, Arai K, Yamakawa T, Chen Y.-J, Salter MM, Yamashita Y. Adv. Synth. Catal.: 2011; 353 1927
11. Terada M, Tanaka H, Sorimachi K. J. Am. Chem. Soc.: 2009; 131 3430
12. Zhang Q.-W, Fan C.-A, Zhang H.-J, Tu Y.-Q, Zhao Y.-M, Gu P, Chen Z.-M. Angew. Chem. Int. Ed.: 2009; 48 8572
13. Corić I, Müller S, List B. J. Am. Chem. Soc.: 2010; 132 17370
14. Corić I, Vellalath S, List B. J. Am. Chem. Soc.: 2010; 132 8536
15. Corić I, List B. Nature (London): 2012; 483 315
16. TenBrink RE, Bergh CL, Duncan JN, Harris DW, Huff RM, Lahti RA, Lawson CF, Lutzke BS, Martin IJ, Rees SA, Schlachter SK, Sih JC, Smith MW. J. Med. Chem.: 1996; 39 2435
17. Albrecht U, Lalk M, Langer P. Bioorg. Med. Chem.: 2005; 13 1531
18. Alberts A, Chen J, Kuron G, Hunt V, Huff J, Hoffman C, Rothrock J, Lopez M, Joshua H, Harris E, Patchett A, Monaghan R, Currie S, Stapley E, Albers-Schonberg G, Hensens O, Hirshfield J, Hoogsteen K, Liesch J, Springer J. Proc. Natl. Acad. Sci. U.S.A.: 1980; 77 3957
19. Cozzi PierG, Hilgraf R, Zimmermann N. Eur. J. Org. Chem.: 2004; 4095
20. Pu L. Tetrahedron: 2003; 59 9873
21. Yang F, Xi P, Yang L, Lan J, Xie R, You J. J. Org. Chem.: 2007; 72 5457
22. Trost BM, Chan VS, Yamamoto D. J. Am. Chem. Soc.: 2010; 132 5186
23. Takita R, Yakura K, Ohshima T, Shibasaki M. J. Am. Chem. Soc.: 2005; 127 13760
24. Koyuncu H, Dogan Ö. Org. Lett.: 2007; 9 3477
25. Ito J.-I, Asai R, Nishiyama H. Org. Lett.: 2010; 12 3860
26. Frantz DE, Fässler R, Carreira EM. J. Am. Chem. Soc.: 2000; 122 1806
27. Boyall D, Frantz DE, Carreira EM. Org. Lett.: 2002; 4 2605
28. Asano Y, Ito H, Hara K, Sawamura M. Organometallics: 2008; 27 5984
29. Asano Y, Hara K, Ito H, Sawamura M. Org. Lett.: 2007; 9 3901
30. Anand NK, Carreira EM. J. Am. Chem. Soc.: 2001; 123 9687
31. Zhou S, Chen C.-R, Gau H.-M. Org. Lett.: 2010; 12 48
32. Liu L, Wang R, Kang Y.-F, Cai H.-Q, Chen C. Synlett: 2006; 1245
33. Chen C, Hong L, Xu Z.-Q, Liu L, Wang R. Org. Lett.: 2006; 8 2277
34. Ahamed M, Todd MH. Eur. J. Org. Chem.: 2010; 5935
35. Black DA, Beveridge RE, Arndtsen BA. J. Org. Chem.: 2008; 73 1906
36. Sun Z, Yu S, Ding Z, Ma D. J. Am. Chem. Soc.: 2007; 129 9300
37. Taylor AM, Schreiber SL. Org. Lett.: 2006; 8 143
38. Downey C, Mahoney B, Lipari V. J. Org. Chem.: 2009; 74 2904
39. Downey C, Johnson M, Tracy K. J. Org. Chem.: 2008; 73 3299