Enantioselective O-nitroso aldol reaction of silyl enol ethers

Angewandte Chemie - International Edition

Volumn 47, Issue 20, 2008, Pages 3795-3797

  Kawasaki, Masanori ^a   Li, Pingfan ^a   Yamamoto, Hisashi ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

Aldol reaction; Asymmetric catalysis; Enantioselectivity; Hydroxylation; Regioselectivity

Indexed keywords

CHEMICAL REACTIONS; ETHERS; MATHEMATICAL TRANSFORMATIONS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; SILANES; SILVER;

ALDOL REACTION; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVITY; HYDROXYLATION; REGIOSELECTIVITY;

DIFFERENCE EQUATIONS;

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; ETHER DERIVATIVE; NITROSO DERIVATIVE; SILVER;

ARTICLE; CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; ETHERS; NITROSO COMPOUNDS; SILVER; STEREOISOMERISM;

EID: 45549084536     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705679     Document Type: Article

References (25)

1. For reviews on α hydroxylation, see: a) F. A. Davis, B. C. Chen, Chem. Rev. 1992, 92, 919;
2. b) F. A. Davis, B. C. Chen in Houben-Weyl: Methods of Organic Chemistry, Vol. E21 (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme, Stuttgart, 1995, p. 4497;
3. c) P. Zhou, B. C. Chen, F. A. Davis in Asymmetric Oxidation Reactions (Ed.: T. Katsuki), Oxford University Press, Oxford, 2001, p. 128.
4. For general reviews of nitroso chemistry, see: a) H. Yamamoto, M. Kawasaki, Bull. Chem. Soc. Jpn. 2007, 80, 595;
5. b) H. Yamamoto, N. Momiyama, Chem. Commun. 2005, 3514;
6. c) P. Merino, T. Tejero, Angew. Chem. 2004, 116, 3055;
7. Angew. Chem. Int. Ed. 2004, 43, 2995.
8. a) N. Momiyama, Y. Yamamoto, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 1190;
9. b) N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2005, 127, 1080;
10. c) N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5360;
11. d) N. Momiyama, H. Torii, S. Saito, H. Yamamoto, Proc. Natl. Acad. Sci. USA 2004, 101, 5374;
12. e) N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2003, 125, 6038.
13. For the synthesis of pentamethyldisilanyl enol ethers, see: a) R. F. Cunico, Synth. Inorg. Met.-Org. Chem. 1985, 290, 33;
14. b) K. K. Laali, G. Maas, M. Gimmy, J. Chem. Soc. Perkin Trans. 2 1993, 1387.
15. Several chiral phosphine ligands, including binap (2,2′- bis(diphenylphosphanyl)-1,1′-binaphthyl), segphos ((4,4′-bi-1,3- benzodioxole)-5,5′-diylbis(diphenylphosphane)), tol-binap (2,2′-bis(di-p-tolylphosphanyl)-1,1′-binaphthyl), and xylyl-solphos (7,7′-bis(di-3,5-xylylphosphanyl)-3,3′,4,4′- tetrahydro-4,4′-dimethyl-8,8′-bi(2H-1,4-benzoxazine)) were tested; however, mixtures of products were obtained with moderate ee values.
16. Although the pentamethyldisilanyl group is bulky, it makes enol ethers more reactive, because the Si-Si bond donates electrons to the π system by hyperconjugation; for similar examples, see: a) M. Akakura, M. B. Boxer, H. Yamamoto, ARKIVOC 2007, 337;
17. b) H. Yamamoto, M. B. Boxer, Chimia 2007, 61, 279;
18. c) M. B. Boxer, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 2762;
19. d) M. B. Boxer, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 48;
20. e) M. B. Boxer, H. Yamamoto, Org. Lett. 2005, 7, 3127.
21. For the synthesis of chiral phosphite ligands, see: a) V. E. Albrow, A. J. Blake, R. Fryatt, C. Wilson, S. Woodward, Eur. J. Org. Chem. 2006, 2549;
22. b) M. Reetz, G. Mehler, Angew. Chem. 2000, 112, 4047;
23. Angew. Chem. Int. Ed. 2000, 39, 3889.
24. For the preparation of chiral silyl enol ethers, see: R. Shintani, N. Tokunaga, H. Doi, T. Hayashi, J. Am. Chem. Soc. 2004, 126, 6240.
25. The configuration of the products was confirmed by comparison with literature data after cleavage of the N-O bond: E. Vedejs, D. A. Engler, J. E. Telschow, J. Org. Chem. 1978, 43, 188.