Synthesis of enantiopure 1-arylprop-2-en-1-ols and their tert-butyl carbonates

Journal of Organic Chemistry

Volumn 73, Issue 22, 2008, Pages 9148-9150

  Štambaský, Jan ^a,b   Malkov, Andrei V ^a,c   Kočovský, Pavel ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b NovaEnergo ^*  (Czech Republic)

^c LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS;

CHEMICAL EQUATIONS; DERIVATIZATION; ENANTIOPURE; SYNTHESIS OF;

CARBONATES;

CARBONIC ACID; LIGAND; TERT BUTYL CARBONATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 56449110112     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801874r     Document Type: Article

References (27)

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3. For an overview of catalysis by other metals, see: (c) Kočovský, P.; Malkov, A. V.; Vyskočil, Š.; Lloyd-Jones, G. C. Pure Appl. Chem. 1999, 71, 1425.
4. (d) Kočovský, P.; Malkov, A. V. Pure Appl. Chem. 2008, 80, 953.
5. 3-complex 2 (ref 1). However, this may not always be the case, as known from the elucidation of the "memory effect": (a) Lloyd-Jones, G. C.; Stephen, S. C.; Murray, M.; Butts, C. P.; Vyskočil; Š.; Kočovský, P. Chem. - Eur. J. 2000, 6, 4348.
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11. 3-complex 2 is formed via inversion of configuration (ref 1). For the retention pathway, see: (a) Starý, I.; Kočovský, P. J. Am. Chem. Soc. 1989, 111, 4981.
12. (b) Farthing, C. N.; Kočovský, P. J. Am. Chem. Soc. 1998, 120, 6661, and refs cited therein.
13. 3-complex 2 has been shown to arise via retention of configuration: (a) Dvořák, D.; Starý, I.; Kočovský, P. J. Am. Chem. Soc. 1995, 117, 6130.
14. (b) Lloyd-Jones, G. C.; Krska, S. W.; Hughes, D. L.; Gouriou, L.; Bonnet, V. D.; Jack, K.; Sun, Y.; Reamer, R. A. J. Am. Chem. Soc. 2004, 126, 702.
15. The Rh- and Ir-catalyzed allylic substitution is known to give products of overall retention of configuration. However, the stereochemistry of the individual steps has not been elucidated: (a) Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581.
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20. The stereochemistry of the formation of the molybdenum complex 2 (M = Mo) from a chiral substrate 3, carried out in the presence of a chiral ligand, is controlled predominantly by the ligand. An isomerization in the case of a "mismatched" combination of 3 and L* has been demonstrated, so that even a racemic substrate 3 can be converted into a substitution product with high enantioselectivity: Malkov, A. V.; Starý, I.; Gouriou, L.; Lloyd-Jones, G. C.; Langer, V.; Spoor, P.; Vinader, V.; Kočovský, P. Chem. - Eur. J. 2006, 12, 6910.
21. Stoner, E. J.; Peterson, M. J.; Allen, M. S.; DeMattei, J. A.; Haight, A. R.; Leanna, M. R.; Patel, S. R.; Plata, D. J.; Premchandran, R. H.; Rasmussen, M. J. Org. Chem. 2003, 68, 8847-8852.
22. 8 featured the reaction of 3-quinolinecarboxaldehyde, which is closely related to 4j, our only successful substrate. As we have now demonstrated, this method is far from being general.
23. 13C NMR spectroscopy.
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27. The configuration was corroborated by the reaction of the carbonates 5 in a transition-metal-catalyzed allylic substitution with an enantiomerically pure alcohol, whose absolute configuration was known. Details of this chemistry will be revealed in due course. For a preliminary account, see ref 1d.