Studies towards 1,3-diol units starting from syn β-hydroxy acylsilanes

Tetrahedron Letters

Volumn 55, Issue 2, 2014, Pages 365-368

  Pavankumar Reddy, Gangireddy ^a   Srirama Murthy, Akondi ^a,b   Satyanarayana Reddy, J ^a,b   Das, Saibal ^b   Roisnel, Thierry ^a   Yadav, Jhillu S ^b   Chandrasekhar, Srivari ^b   Grée, René ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1,3 Diols; Acyl silanes; Aldol; Silicon; Tischenko

Indexed keywords

1,3 DIOL; FLUORIDE; PHENYL GROUP; SILANE DERIVATIVE; SILICON; SYN BETA HYDROXY ACYLSILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DESILYLATION; GRIGNARD REACTION; HYDROGEN BOND; ISOMERIZATION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84890787752     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.11.034     Document Type: Article

References (29)

1. A.F. Patrocinio, and P.J.S. Moran J. Braz. Chem. Soc. 12 2001 7 31
2. P.C.B. Page, and M.J. McKenzie Product Subclass 25: Acylsilanes Fleming Science of Synthesis Vol. 4 2001 Thieme Stuttgart 513 568
3. M.N. Garrett, and J.S. Johnson Product Subclass 4: Silicon compound I. Fleming, Science of Synthesis 2012, Vol. 4 Stuttgart Thieme 1 85
4. H.-J. Zhang, D.L. Priebbenow, and C. Bolm Chem. Soc. Rev. 42 2013 8540 8571
5. G.R. Boyce, S.N. Grezler, J.S. Johnson, X. Linghu, J.T. Malinovski, D.A. Nicewicz, A.D. Satterfield, D.C. Schmitt, and K.M. Steward J. Org. Chem. 77 2012 4503 4515
6. (a) For syntheses of β-hydroxy acylsilanes via aldol reactions using acyl silane enolates, see: D. Schinzer Synthesis 1989 179 181
7. Y. Horiuchi, M. Taniguchi, K. Oshima, and K. Utimoto Tetrahedron Lett. 36 1995 5353 5356
8. (c) For Mukaiyama aldol reactions, see: M. Honda, W. Oguchi, M. Segi, and T. Nakajima Tetrahedron 58 2002 6815 6823
9. (d) For syntheses through tandem aldol-Tishchenko reactions, see: M. Honda, R. Iwamoto, Y. Nogami, and M. Segi Chem. Lett. 34 2005 466 467
10. (e) See also M. Honda, and M. Segi Yuki Gosei Kagaku Kyokaishi 68 2010 601 613
11. G. PavanKumar Reddy, J. Satyanarayana Reddy, S. Das, T. Roisnel, J.S. Yadav, S. Chandrasekhar, and R. Grée Org. Lett. 15 2013 1524 1527
12. Akondi Srirama Murthy, T. Roisnel, S. Chandrasekhar, and R. Grée Synlett 2013 2216 2220
13. A.G. Brook J. Am. Chem. Soc. 80 1958 1886 1889
14. A.G. Brook Acc. Chem. Res. 7 1974 77 84
15. W.H. Moser Tetrahedron 57 2001 2065 2084
16. A. Degl'Innocenti, S. Pike, D.R.M. Walton, G. Seconi, A. Ricci, and M.J.C.S. Fiorenza Chem. Commun. 1980 1201 1202
17. K. Morihata, Y. Horiuchi, M. Taniguchi, K. Oshima, and K. Utimoto Tetrahedron Lett. 36 1995 5555 5558
18. M. Honda, N. Ohkura, S. Saisyo, M. Segi, and T. Nakajima Tetrahedron 59 2003 8203 8212
19. J.D. Buynak, J.B. Strickland, G.W. Lamb, D. Khasnis, S. Modi, D. Williams, and H. Zhang J. Org. Chem. 56 1991 7076 7083
20. A. Abae, E. Brenna, C. Fuganti, F.G. Gatti, T. Giovenzana, L. Malpezzi, and S. Serra J. Org. Chem. 70 2005 1281 1290 and references cited therein
21. CCDC 949455 contain the supplementary crystallographic data for compound 2a. CCDC 949456 contain the supplementary crystallographic data for compound 5. CCDC 949457 contain the supplementary crystallographic data for compound 8. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
22. M. Nakada, Y. Urano, S. Kobayashi, and M. Ohno J. Am. Chem. Soc. 110 1988 4826 4827
23. B.F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, C. Nanni, and A. Ricci Tetrahedron Lett. 39 1998 6737 6740
24. B.F. Bonini, M. Comes-Franchini, M. Fochi, J. Gawronski, G. Mazzanti, C. Nanni, A. Ricci, and G. Varchi Eur. J. Org. Chem. 1999 437 445
25. P.M. Bodnar, J.T. Shaw, and K.A. Woerpel J. Org. Chem. 62 1997 5674 5675
26. I. Simpura, and N. Nevalainen Tetrahedron 59 2003 7535 7546
27. K. Rohr, R. Herrre, and R. Mahrwald Org. Lett. 7 2005 4499 4501
28. Noteworthy to mention that magnesium enolates are known to afford anti aldol products: (a) C.H. Heatcock, and S. Arseniyadis Tetrahedron Lett. 26 1985 6009 6012
29. K.A. Swiss, W.-B. Choi, D.C. Liotta, A.F. Abdel-Magid, and C. Maryanoff J. Org. Chem. 56 1991 5978 5980