Enantiodivergent conversion of chiral secondary alcohols into tertiary alcohols

Nature

Volumn 456, Issue 7223, 2008, Pages 778-783

  Stymiest, Jake L ^a   Bagutski, Viktor ^a   French, Rosalind M ^a   Aggarwal, Varinder K ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKENYL GROUP; ALKYL GROUP; BORONIC ACID DERIVATIVE; CARBON; HYDROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ALCOHOL; CHEMICAL COMPOSITION; ESTER; HYDROGEN; MOLECULAR ANALYSIS; POLYMER; REACTION KINETICS;

ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; IMAGE DISPLAY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 57649120956     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature07592     Document Type: Article

References (30)

1. Crossley, R. The relevance of chirality to the study of biological activity. Tetrahedron 48, 8155-8178 (1992).
2. Thayer, A. M. Centering on chirality. Chem. Eng. News 85, 11-19 (2007).
3. Pu, L. & Yu, H.-B. Catalytic asymmetric organozinc additions to carbonyl compounds. Chem. Rev. 101, 757-824 (2001).
4. Noyori, R. & Hashiguchi, S. Asymmetric transfer hydrogenation catalysed by chiral ruthenium complexes. Acc. Chem. Res. 30, 97-102 (1997).
5. Riant, O. & Hannedouche, J. Asymmetric catalysis for the construction of quaternary carbon centres: nucleophilic addition on ketones and ketimines. Org. Biomol. Chem. 5, 873-888 (2007).
6. Christoffers, J. & Baro, A. (eds) Quaternary Stereocentres: Challenges and Solutions for Organic Synthesis (Wiley-VCH, 2005).
7. Corey, E. J. & Guzman-Perez, A. The catalytic enantioselective construction of molecules with quaternary carbon stereocentres. Angew. Chem. Int. Ed. 37, 388-401 (1998).
8. Shibasaki, M.&Kanai, M. Asymmetric synthesis of tertiary alcohols and α-tertiary amines via Cu-catalysed C-C bond formation to ketones and ketimines. Chem. Rev. 108, 2853-2873 (2008).
9. Thiemann, W. H.-P. Homochirality of the evolution of biospheres. Jpn Soc. Biol. Sci. Space 12, 73-77 (1998).
10. Levin, G. B., Miller, J. D., Straat, P. A., Lodder, R. A. & Hoover, R. B. Detecting life and biology-related parameters on Mars. 〈http://mars.spherix.com/IEEE%20Pape-FINAL.pdf〉 (2006).
11. D'Amato, R. J., Loughnan, M. S., Flynn, E. & Folkman, J. Thalidomide is an inhibitor of angiogenesis. Proc. Natl Acad. Sci. USA 91, 4082-4085 (1994).
12. Rouhi, M. Top pharmaceuticals: thalidomide. Chem. Eng. News 83, 122-123 (2005).
13. Kolb, H. C., VanNieuwenhze, M. S. & Sharpless, K. B. Catalytic asymmetric dihydroxylation. Chem. Rev. 94, 2483-2547 (1994).
14. 3(thf)] to ketones catalyzed by a titanium(IV) catalyst of (S)-binol. Angew. Chem. Int. Ed. 46, 5373-5376 (2007).
15. Ramón, D. J. & Yus, M. First enantioselective addition of dialkylzinc to ketones promoted by titanium(IV) derivatives. Tetrahedr. Lett. 39, 1239-1242 (1998).
16. Betancort, J. M., García, C. & Walsh, P. J. Development of the first practical catalyst for the asymmetric addition of alkyl- and arylzinc reagents to ketones. Synlett 2004, 749-760 (2004).
17. Hoppe, D., Carstens, A. & Kramer, T. Generation of a configurationally stable chiral benzyllithium derivative, and the capricious stereochemistry of its electrophilic substitution. Angew. Chem. Int. Edn Engl. 29, 1424-1425 (1990).
18. Carstens, A. & Hoppe, D. Generation of a configurationally stable, enantioenriched α-oxy-α-methylbenzyllithium: stereodivergence of its electrophilic substitution. Tetrahedron 50, 6097-6108 (1994).
19. Matteson, D. S. & Hurst, G. D. Asymmetric synthesis of tertiary alcohols from a-halo boronic esters. Heteroatom Chem. 1, 65-74 (1990).
20. Matteson, D. S. α-Halo boronic esters in asymmetric synthesis. Tetrahedron 54, 10555-10607 (1998).
21. Hoppe, D. & Hense, T. Enantioselective synthesis with lithium/(-)-sparteine carbanion pairs. Angew. Chem. Int. Edn Engl. 36, 2282-2316 (1997).
22. Stymiest, J. L., Dutheuil, G., Mahmood, A. & Aggarwal, V. K. Lithiated carbamates: chiral carbenoids for iterative homologation of boranes and boronic esters. Angew. Chem. Int. Ed. 46, 7491-7494 (2007).
23. Fujii, A., Hashiguchi, S., Uematsu, N., Ikariya, T. & Noyori, R. Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture. J. Am. Chem. Soc. 118, 2521-2522 (1996).
24. Aggarwal, V. K., Fang, G. Y., Ginesta, X., Howells, D. & Zaja, M. Toward an understanding of the factors responsible for the 1,2-migration of alkyl groups in borate-complexes. Pure Appl. Chem. 78, 215-229 (2006).
25. Fang, G. Y. et al. Asymmetric sulfur ylide reactions with boranes: scope and limitations, mechanism and understanding. J. Am. Chem. Soc. 129, 14632-14639 (2007).
26. Derwing, C., Frank, H. & Hoppe, D. Chiral benzyllithium compounds: high configurative stability of (R)- and (S)-1-lithioindan-1-yl N,N-diisopropylcarbamate and unexpected stereochemical course of the substitution reactions. Eur. J. Org. Chem. 1999, 3519-3524 (1999).
27. Jeon, S.-J., Li, H., García, C., LaRochelle, L. K. & Walsh, P. Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones. J. Org. Chem. 70, 448-455 (2005).
28. Jeon, S.-J., Ji, H. & Walsh, P. J. A green chemistry approach to a more efficient asymmetric catalyst: solvent-free and highly concentrated alkyl additions to ketones. J. Am. Chem. Soc. 127, 16416-16425 (2005).
29. Forrat, V. J., Ramón, D. J. & Yus, M. Chiral tertiary alcohols from a trans-1-arenesulfonyl-amino-2-isoborneolsulfonylaminocyclohexane- catalyzed addition of organozincs to ketones. Tetrahed. Asymm. 16, 3341-3344 (2005).
30. 3 · 2 LiCl) for the improved addition of organomagnesium reagents to carbonyl compounds. Angew. Chem. Int. Ed. 45, 497-500 (2006).