SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 12: 3454 - 3459

DOI: https://doi.org/10.6023/cjoc201904081

Studies on the Stereoselective Synthesis of Functionalized Allylsilane Compounds

  • Jiang Quan ,
  • He Ling ,
  • Li Weidong
Expand
  • a Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331

Received date: 2019-04-30

  Revised date: 2019-07-25

  Online published: 2019-08-30

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21672030, 21702023).

Fold

Abstract

Allylsilanes have emerged as synthetically useful intermediates that can undergo a variety of chemical transformations and have been found versatile applications in C-C bond construction as well as in preparation of complex molecules. Exploration on the stereoselective route to functionalized allylsilanes is of great significance for the development of organic synthetic methodology. An efficient pathway to a series of novel alkoxy-substituted homoiodio-allylsilanes via the Julia olefination of silylmethyl cyclopropyl carbinols was described. Carbinols derived from cyclopropyl aryl ketone were evidenced to be superiorer in controlling the stereoselectivity of the products than the alkyl equivalents.

Key words： allylsilane; Julia olefination; cyclopropyl carbinol; Grignard reagent

Cite this article

Jiang Quan , He Ling , Li Weidong . Studies on the Stereoselective Synthesis of Functionalized Allylsilane Compounds[J]. Chinese Journal of Organic Chemistry, 2019 , 39(12) : 3454 -3459 . DOI: 10.6023/cjoc201904081

References

[1] Sommer, L. H.; Tyler, L. J.; Whitmore, F. C. J. Am. Chem. Soc. 1948, 70, 2872.
[2] For recent reviews, see:(a) Ramachandran, P. V.; Nicponski, D. R.; Gagare, P. D. In Comprehensive Organic Synthesis II, Vol. 2, Eds.:Knochel, P.; Molander, G. A., Elsevier, Amsterdam, 2014, p. 72.
(b) Díez-Poza, C.; Barbero, A. Eur. J. Org. Chem. 2017, 2017, 4651.
(c) Schmidt, A. W.; Knölker, H.-J. Synlett 2010, 2207.
(d) Chabaud, L.; James, P.; Landais, Y. Eur. J. Org. Chem. 2004, 3173.
(e) Barbero, A.; Pulido, F. J. Acc. Chem. Res. 2004, 37, 817.
(f) Méndez, M.; Echavarren, A. M. Eur. J. Org. Chem. 2002, 15.
(g) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
[3] Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375.
[4] For reviews on the synthesis of allylsilanes see 2a, and also see:(a) Sarkar, T. K. Synthesis 1990, 969.
(b) Sarkar, T. K. Synthesis 1990, 1101.
(c) Suginome, M.; Ito, Y. J. Organomet. Chem. 2003, 680, 43.
(d) Barbero, A.; Pulido, F. J. Synthesis 2004, 779.
[5] Han, J. W.; Hayashi, T. Tetrahedron: Asymmetry 2010, 21, 2193 and references therein.
[6] (a) Chan, T. H.; Wang, D. Chem. Rev. 1992, 92, 995.
(b) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293. For selected examples on transformations of chiral allylsilanes, see:
(c) Hayashi, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 4963.
(d) Wang, D. Chin. J. Org. Chem. 2001, 21, 1090(in Chinese). (王东, 有机化学, 2001, 21, 1090.)
(e) Wu, J.; Pu, Y.; Panek, J. S. J. Am. Chem. Soc. 2012, 134, 18440.
[7] (a) Li, W.-D. Z.; Yang, J.-H. Org. Lett. 2004, 6, 1849.
(b) Yang, J. H.; Li, W. D. Z. Chin. Chem. Lett. 2005, 16, 433.
[8] (a) Shen, S.-J.; Li, W.-D. Z. J. Org. Chem. 2013, 78, 7112.
(b) Gao, H.-T.; Wang, B.-L.; Li, W.-D. Z. Tetrahedron 2014, 70, 9436.
[9] Li, W.-D. Z.; Peng, Y. Org. Lett. 2005, 7, 3069.
[10] Lawrence, N. J. Science of Synthesis (Houben-Weyl), Georg Thieme Verlag, Stuttgart, Germany, 2002, pp. 579~594.
[11] Methoxymethyl magnesium chloride is known to be obtained at low temperature but decomposes above -20℃ to release ethylene gas, see:(a) Normant, H.; Castro, B. C. R. Acad. Sci. 1963, 257, 2115.
(b) Castro, B. Bull. Soc. Chim. Fr. 1967, 1533.
[12] Scheiper, B.; Bonnekessel, M.; Krause, H.; Fürstner, A. J. Org. Chem. 2004, 69, 3943.
Options
Outlines

/

〈 〉