Regioselective homologation of bis(boronate) intermediates derived from rhodium-catalyzed diboration of simple alkenes

Synlett

Volumn , Issue 11, 2005, Pages 1749-1751

  Kalendra, Diane M ^a   Dueñes, Rebecca A ^a   Morken, James P ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

Alkenes; Asymmetric catalysis; Boron; Regioselectivity; Silicon

Indexed keywords

1,2 BIS(CATECHOLBORONATE) DERIVATIVE; ALKENE DERIVATIVE; BORONIC ACID DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 22244481890     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-869873     Document Type: Article

References (26)

1. For enantioselective catalytic diboration, see: (a) Morgan, J. B.; Miller, S. P.; Morken, J. P. J. Am. Chem. Soc. 2003, 125, 8702.
2. For Rh-catalyzed diboration of alkenes, see: (b) Baker, R. T.; Nguyen, P.; Marder, T. B.; Westcott, S. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1336.
3. (c) Dai, C.; Robins, E. G.; Scott, A. J.; Clegg, W.; Yufit, D. S.; Howard, J. A. K.; Marder, T. B. Chem. Commun. 1998, 1983.
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9. (a) Hydrogen peroxide and NaOH is most commonly used for oxidation of C-B bonds: Zweifel, G.; Brown, H. C. Org. React. 1963, 13, 1.
10. (b) A number of other oxidants have also been employed for this purpose, see: Kabalka, G. W.; Wadgaonkar, P. P.; Shoup, T. M. Organometallics 1990, 9, 1316; and references cited therein.
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23. (i) For diastereoselective homologation of C-B bonds with prochiral homologation reagents, see: Hoffmann, R. W.; Stiasny, H. C. Tetrahedron Lett. 1995, 36, 4595.
24. 3 and extracted with EtOAc. The crude material was purified by silica gel chromatography (3:1 hexanes-EtOAc) to provide 25 mg (49% yield) of pure 4,4-dimethyl-1-(trimethylsilyl)pentane-1,3-diol.
25. 2O, the solution was concentrated and the crude material purified on silica gel (2:1 hexanes-EtOAc) to give 9.4 mg (38% yield) of 4,4-dimethyl-1,3-pentanediol.
26. Soderquist, J. A.; Najafi, M. R. J. Org. Chem. 1986, 51, 1330.