Enantioselective [2,3]-Wittig rearrangement via sparteine-mediated lateral metalation of N,N-dialkyl-o-allyloxymethylbenzamides and o-substituted benzyl prenyl ethers

Synlett

Volumn , Issue 12, 1998, Pages 1429-1431

  Kawasaki, Takeshi ^a   Kimachi, Tetsutaro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001872894     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1978     Document Type: Article

References (21)

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14. Clark, R. D.; Jahangir, A. Org. React.; John Wiley & Sons, Inc.: N. Y., 1995; Vol. 47., 1.
15. (a) Thayumanavan, S.; Basu, A.; Beak, P. J. Am. Chem. Soc. 1997, 119, 8209.
16. (b) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552.
17. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
18. 1H-NMR, HRMS) data consistent with the depicted structure.
19. 4Cl aq. and extracted with AcOEt. Purification by flash chromatography afforded the compounds listed in Table 1 and Table 2.
20. Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 3136.
21. For example, the (S) absolute configuration of 4a (Table 1, entry 4) was determined as follows. (Chemical Equation Presented)