A unique approach to aldol products for the creation of all-carbon quaternary stereocentres

Nature Chemistry

Volumn 1, Issue 2, 2009, Pages 128-132

  Das, Jaya Prakash ^a   Chechik, Helena ^a   Marek, Ilan ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; BIOLOGICAL PRODUCT; CARBON;

ARTICLE; CHEMISTRY; CONFORMATION; HYDROLYSIS; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; BIOLOGICAL PRODUCTS; CARBON; CRYSTALLOGRAPHY, X-RAY; HYDROLYSIS; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 67949106332     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.131     Document Type: Article

References (21)

1. Corey, E. J. & Guzman-Perez, A. The catalytic enantioselective construction of molecules with quaternary carbon stereocenters. Angew. Chem. Int. Ed. 37, 388-401 (1998).
2. Trost, B. M. & Jiang, C. H. Catalytic enantioselective construction of all-carbon quaternary stereocenters. Synthesis 3, 369-396 (2006).
3. Marek, I. A shift in retrosynthetic paradigm. Chem. Eur. J. 14, 7460-7468 (2008).
4. Christoffers, J. & Baro, A. Stereoselective construction of quaternary stereocenters. Adv. Synth. Catal. 347, 1473-1482 (2005).
5. Sklute, G. & Marek, I. New multicomponent approach for the creation of chiral quaternary centers in the carbonyl allylation reactions. J. Am. Chem. Soc. 128, 4642-4649 (2006).
6. Carreira, E. in Modern Carbonyl Chemistry (ed. Otera, J.) Ch. 8, 227-248 (Wiley-VCH, 2001).
7. Manthorpe, J. M. & Gleason, J. L. Stereoselective generation of E- and Z-disubstituted amide enolates. reductive enolate formation from bicyclic thioglycolate lactams. J. Am. Chem. Soc. 123, 2091-2092 (2001).
8. Yamago, S., Machii, D. & Nakamura, E. Simple diastereoselectivity of the aldol reaction of persubstituted enolates. Stereoselective construction of quaternary centers. J. Org. Chem. 56, 2098-2106 (1991).
9. Qin, Y. C., Stivala, C. E. & Zakarian, A. Acyclic stereocontrol in the Ireland-Claisen rearrangement of α-branched esters. Angew. Chem. Int. Ed. 46, 7466-7469 (2007).
10. Sklute, G. & Marek, I. Creation of quaternary stereocenters in carbonyl allylation reactions. Chem. Commun. 1683-1691 (2007).
11. Häner, R., Laube, T. & Seebach, D. Regio- and diastereoselective preparation of aldols from α-branched ketone enolates generated from BHT ester enolates and organolithium reagents: In-situ generation and trapping of ketenes from ester enolates. J. Am. Chem. Soc. 107, 5396-5403 (1985).
12. Sidduri, A. R., Rozema, M. J. & Knochel, P. Selective mono- and polymethylene homologations of copper reagents using (iodomethyl)zinc iodide, J. Org. Chem. 58, 2694-2713 (1993).
13. Normant, J. F. & Alexakis, A. Carbometallation (C-metallation) of alkynes: Stereospecific synthesis of alkenyl derivatives. Synthesis 841-870 (1981).
14. Kolodney, G., Sklute, G., Perrone, S., Knochel, P. & Marek, I. Diastereodivergent synthesis of enantiomerically pure homoallylic amine derivatives containing quaternary carbon stereocenters. Angew. Chem. Int. Ed. 46, 9291-9294 (2007).
15. Frederick, M. O. et al. A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides. J. Am. Chem. Soc. 123, 2368-2369 (2003).
16. Feuillet, F. J. P., Niyadurupola, D. G., Green, R., Cheeseman, M. & Bull, S. D. Stereoselective rearrangement of β-hydroxy-N- acyloxazolidin-2-ones to afford N-2-hydroxyethyl-1,3-oxazinane-2,4- diones. Synlett 1090-1094 (2005).
17. Chechik-Lankin, H., Livshin, S. & Marek, I. Regiocontrolled carbometallation reactions of ynamides. Synlett 2098-2100 (2005).
18. Charette, A. B. et al. Preparation, solid-state structure, and synthetic applications of isolable and storable haloalkylzinc reagents. J. Am. Chem. Soc. 122, 4508-4509 (2000).
19. 3 organozinc carbenoid homologation in organic synthesis. Tetrahedron 58, 9463-9475 (2002).
20. Overman, L. E. & Bell, K. L. Enantiospecific total synthesis of dendrobatid toxin 251D. A short chiral entry to the cardiac-active pumiliotoxin A alkaloids via stereospecific iminium ion-vinylsilane cyclizations. J. Am. Chem. Soc. 103, 1851-1853 (1981).
21. Mase, N., Tanaka, F. & Barbas, C. F. III Synthesis of β-hydroxyaldehydes with stereogenic quaternary carbon centers by direct organocatalytic asymmetric aldol reactions. Angew. Chem. Int. Ed. 43, 2420-2423 (2004).