Asymmetric Conjugate Addition of Alkylzirconocenes to Cyclopent-4-ene-1,3-dione Monoacetals

Synthesis (Germany)

Volumn 47, Issue 15, 2015, Pages 2217-2222

  Rideau, Emeline ^a   Mäsing, Florian ^a   Fletcher, Stephen P ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

acetals; addition reactions; asymmetric catalysis; copper; organometallic reagents

Indexed keywords

CATALYSIS; COPPER; ENANTIOSELECTIVITY; FUNCTIONAL GROUPS; ORGANOMETALLICS;

ACETALS; ASYMMETRIC CATALYSIS; ASYMMETRIC CONJUGATE ADDITION; ENANTIOSELECTIVE CONJUGATE ADDITION; FIVE-MEMBERED RINGS; HIGH ENANTIOSELECTIVITY; ORGANOMETALLIC REAGENT; SINGLE ENANTIOMERS;

ADDITION REACTIONS;

4 (6 CHLOROHEXYL) 8,8 DIPHENYL 6,10 DIOXASPIRO[4.5]DECAN 2 ONE; 4 HEXYL 8,8 DIPHENYL 6,10 DIOXASPIRO[4.5]DECAN 2 ONE; 4 [4 (BENZYLOXY)BUTYL] 8,8 DIPHENYL 6,10 DIOXASPIRO[4.5]DECAN 2 ONE; 8,8 DIMETHYL 4 (4 PHENYLBUTYL) 6,10 DIOXASPIRO[4.5]DECAN 2 ONE; 8,8 DIPHENYL 4 (2 PHENYLETHYL) 6,10 DIOXASPIRO[4.5]DECAN 2 ONE; 8,8 DIPHENYL 4 (4 PHENYLBUTYL) 6,10 DIOXASPIRO[4.5]DECAN 2 ONE; 8,8 DIPHENYL 4 [3 (TRIMETHYLSILYL)PROPYL] 6,10 DIOXASPIRO[4.5]DECAN 2 ONE; ACETAL; ALKYLZIRCONOCENE DERIVATIVE; CHLOROTRIMETHYLSILANE; CYCLOPENT 4 ENE 1,3 DIONE MONOACETAL DERIVATIVE; CYCLOPENTANONE DERIVATIVE; DICHLOROMETHANE; ETHER; TERT BUTYL METHYL ETHER; TOLUENE; UNCLASSIFIED DRUG; ZIRCONOCENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONJUGATE; ENANTIOSELECTIVITY; LOW TEMPERATURE; ROOM TEMPERATURE; SOLVENT EFFECT; SYNTHESIS;

EID: 84937516319     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0034-1379928     Document Type: Article

References (25)

1. Harutyunyan S. R., den Hartog T., Geurts K., Minnaard A. J., Feringa B. L. Chem. Rev.: 2008; 108 2824
2. Copper-Catalyzed Asymmetric Synthesis. Alexakis A., Krause N., Woodward S. Wiley-VCH Weinheim: 2014
3. Krause N., Hoffmann-Röder A. Synthesis: 2001; 171
4. Hayashi T., Yamasaki K. Chem. Rev.: 2003; 103 2829
5. Alexakis A., Bäckvall J. E., Krause N., Pàmies O., Diéguez M. Chem. Rev.: 2008; 108 2796
6. Maksymowicz R. A., Bissette A. J., Fletcher S. P. Chem. Eur. J.: 2015; 21 5668
7. Feringa B. L. Acc. Chem. Res.: 2000; 33 346
8. Krause N. Angew. Chem. Int. Ed.: 1998; 37 283
9. Kanai M., Nakagawa Y., Tomioka K. Tetrahedron: 1999; 55 3843
10. Degrado S. J., Mizutani H., Hoveyda A. H. J. Am. Chem. Soc.: 2001; 123 755
11. Brown M. K., Hoveyda A. H. J. Am. Chem. Soc.: 2008; 130 12904
12. Jansen D. J., Shenvi R. A. J. Am. Chem. Soc.: 2013; 135 1209
13. Sunazuka T., Hirose T., Shirahata T., Harigaya Y., Hayashi M., Komiyama K., Omura S., Smith A. B. J. Am. Chem. Soc.: 2000; 122 2122
14. Arnold L. A., Naasz R., Minnaard A. J., Feringa B. L. J. Am. Chem. Soc.: 2001; 123 5841
15. Maksymowicz R. M., Roth P. M. C, Fletcher S. P. Nat. Chem.: 2012; 4 649
16. Sidera M., Roth P. M. C, Maksymowicz R. M., Fletcher S. P. Angew. Chem. Int. Ed.: 2013; 52 7995
17. Maksymowicz R. M., Roth P. M. C, Thompson A. L., Fletcher S. P. Chem. Commun.: 2013; 49 4211
18. Maksymowicz R. M., Sidera M., Roth P. M. C, Fletcher S. P. Synthesis: 2013; 45 2662
19. Roth P. M. C, Sidera M., Maksymowicz R. M., Fletcher S. P. Nat. Protoc.: 2014; 9 104
20. Maciver E. E., Maksymowicz R. M., Wilkinson N., Roth P. M. C, Fletcher S. P. Org. Lett.: 2014; 16 3288
21. Roth P. M. C, Fletcher S. P. Org. Lett.: 2015; 17 912
22. You H., Rideau E., Sidera M., Fletcher S. P. Nature: 2015; 517 351
23. Mola L., Sidera M., Fletcher S. P. Aust. J. Chem.: 2015; 68 401
24. Sidera M., Fletcher S. P. Chem. Commun.: 2015; 51 5044
25. Arnold L. A., Naasz R., Minnaard A. J., Feringa B. L. J. Org. Chem.: 2002; 67 7244