Regio-controlled pentadienylation of sulfinylimines by pentadienyltin reagent. Efficient Lewis acid activation of 4-methoxyphenylsulfinyl imines

Tetrahedron Letters

Volumn 55, Issue 2, 2014, Pages 510-513

  Nishigaichi, Yutaka ^a   Tsuruta, Shinji ^a   Uenaga, Kenji ^a   Awamura, Tomohiko ^a   Iwamoto, Hidetoshi ^a   Takuwa, Akio ^a  

^a SHIMANE UNIVERSITY   (Japan)

Author keywords

Lewis acid; Pentadienyltin; Regioselectivity; Stereoselectivity; Sulfinyl imine

Indexed keywords

IMINE; LEWIS ACID; REAGENT;

ARTICLE; NUCLEOPHILICITY; ORGANIC CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 84890802195     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.11.093     Document Type: Article

References (16)

1. M. Santelli, and J.-M. Pons Lewis Acids and Selectivity in Organic Synthesis 1996 CRC Press New York p 91
2. A. Yanagisawa, H. Nakashima, Y. Nakatsuka, A. Ishiba, and H. Yamamoto Bull. Chem. Soc. Jpn. 74 2001 1129
3. Y. Nishigaichi, M. Fujimoto, and A. Takuwa Synlett 1994 731
4. Y. Nishigaichi, Y. Hanano, and A. Takuwa Chem. Lett. 27 1998 33
5. Y. Nishigaichi, M. Ishihara, S. Fushitani, K. Uenaga, and A. Takuwa Chem. Lett. 33 2004 108
6. P. Zhou, B.-C. Chen, and F.A. Davis Tetrahedron 60 2004 8003
7. D. Morton, and R.A. Stockman Tetrahedron 62 2006 8869
8. F. Ferreira, C. Botuha, F. Chemla, and A. Pérez-Luna Chem. Soc. Rev. 38 2009 1162
9. M.T. Robak, M.A. Herbage, and J.A. Ellman Chem. Rev. 110 2010 3600
10. Y. Nishigaichi, A. Takuwa, Y. Naruta, and K. Maruyama Tetrahedron 49 1993 7395
11. A.D. Dilman, and S.L. Ioffe Chem. Rev. 103 2003 733
12. It is noteworthy that the applied pentadienyltin reagent consists of an 84:16 mixture of E and Z isomers, respectively. Using pure (Z)-pentadienyltin, the TMSOTf-promoted reaction afforded decreased regioisomeric ratio with a decreased yield; ε/γ = 49:51, 44% yield. It is known that (Z)-pentadienyltin exhibits higher reactivity at its γ-position than at its ε-position Y. Nishigaichi, M. Fujimoto, and A. Takuwa J. Chem. Soc. Perkin Trans. 1 1992 2581
13. Y. Koriyama, A. Nozawa, R. Hayakawa, and M. Shimizu Tetrahedron 58 2002 9621
14. J.C. Gonzalez-Gomez, M. Medjahdi, F. Foubelo, and M. Yus J. Org. Chem. 75 2010 6308
15. 3-promoted reaction (Table 2, entry 6): 3.08 (dt, 8.0, 7.8), 3.84 (3H, s), 4.38 (d, 2.4), 4.42 (dd, 8.0, 1.3), 4.92-5.01 (2H, m), 5.10-5.19 (2H, m), 5.57 (ddd, 17.3, 10.5, 7.1), 5.72 (ddd, 17.1, 10.2, 8.8), 6.99 (2H, d, 9.0), 7.11-7.42 (5H, m), 7.59 (d, 9.0).Minor product (syn-γ) in the InCl3-promoted reaction (Table 2, entry 6): 3.19 (dt, 8.3, 7.1), 3.76 (3H, s), 4.37-4.44 (m), 4.66 (d, 5.6), 5.11-5.21 (4H, m), 5.57-5.76 (2H, m), 6.73 (2H, d, 8.8), 7.11-7.42 (7H, m)
16. P.G.M. Wuts, and T.W. Greene Protective Groups in Organic Synthesis 4th Ed. 2006 Wiley-Interscience Hoboken