Enantioselective synthesis of 3,4-dihydropyran-2-ones by chiral quaternary ammonium phenoxide-catalyzed tandem Michael addition and lactonization

Chemistry Letters

Volumn 35, Issue 1, 2006, Pages 56-57

  Tozawa, Takashi ^a   Yamane, Yoshinobu ^a   Mukaiyama, Teruaki ^a  

^a NONE

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EID: 33645119015     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2006.56     Document Type: Article

References (14)

1. a) T. Tozawa, H. Fujisawa, T. Mukaiyama, Chem. Lett. 2004, 33, 1454.
2. b) T. Tozawa, Y. Yamane, T. Mukaiyama, Chem. Lett. 2005, 34, 514.
3. For recent reviews, see: a) M. J. O'Donnell, Acc. Chem. Res. 2004, 37, 506.
4. b) B. Lygo, B. I. Andrews, Acc. Chem. Res. 2004, 37, 518.
5. c) T. Ooi, K. Maruoka, Acc. Chem. Res. 2004, 37, 526.
6. d) K. Maruoka, T. Ooi, Chem. Rev. 2003, 103, 3013.
7. For the preparation and X-ray crystallographic analysis of quaternary ammonium p-nitrophenoxide, see: E. J. Corey, F. Xu, M. C. Noe, J. Am. Chem. Soc. 1997, 119, 12414.
8. 1H NMR analysis and elemental analysis.
9. B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1997, 38, 8595.
10. 5OH: C, 73.48; H, 5.38; N, 3.12%. Found: C, 73.42; H, 5.45; N, 3.06%.
11. 3) δ 7.67 (d, J = 5.4 Hz, 2H), 7.39-7.14 (m, 8H), 5.93 (d, J = 5.4 Hz, 1H), 3.49 (d, J = 5.4 Hz, 1H), 1.43 (s, 3H), 1.04 (s, 3H). The enantiomeric excess was determined by HPLC analysis using a DAICEL Chiralcel OD-H, hexane/2-propanol = 50/1, λ = 254 nm, flow rate = 1.0 mL/min, retention time = 9.6 min (minor) and 11.2 min (major).
12. a) R. Goddard, H. M. Herzog, M. T. Reetz, Tetrahedron 2002, 58, 7847.
13. b) A. W. Hanson, A. W. McCulloch, A. G. McInnes, Tetrahedron Lett. 1982, 23, 607.
14. N-(9-anthracenylmethyl)-O-[3,5-bis(trifluoromethyl)benzyl]cinchonidinium bromide was prepared according to the reported procedure (see Ref. 3).