Tandem oxidation processes: A combined phosphorus- and sulfur-ylide approach to polysubstituted cyclopropanes

Chemical Communications

Volumn , Issue 17, 2005, Pages 2253-2255

  Oswald, Magalie F ^a   Raw, Steven A ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; CYCLOPROPANE DERIVATIVE; KETOL; MANGANESE DIOXIDE; PHOSPHORUS; SULFUR;

ARTICLE; BIOTRANSFORMATION; CYCLOPROPANATION; MOLECULAR STABILITY; OLEFINATION; OXIDATION; REACTION ANALYSIS;

EID: 18844368813     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b500396b     Document Type: Article

References (11)

1. For examples see: (a) S. A. Raw, M. Reid, E. Roman and R. J. K. Taylor, Synlett, 2004, 819;
2. (b) S. A. Raw, C. D. Wilfred and R. J. K. Taylor, Org. Biomol. Chem., 2004, 2, 788;
3. (c) X. Wei and R. J. K. Taylor, J. Org. Chem., 2000, 65, 616;
4. (d) L. Blackburn and R. J. K. Taylor, Org. Lett., 2001, 3, 1637 and references therein.
5. M. F. Oswald, S. A. Raw and R. J. K. Taylor, Org. Lett., 2004, 6, 3997.
6. (a) G. B. Payne, J. Org. Chem., 1967, 32, 3351;
7. (b) J. Quintana, M. Torres and F. Serratosa, Tetrahedron, 1973, 29, 2065.
8. 2 (10.0 eq.). The mixture was heated to reflux and monitored by TLC. After complete consumption of starting material and all expected intermediates (i.e. cyclopropanecarboxaldehydes or γ-ketocrotonates), the mixture was cooled, filtered through Celite® and concentrated in vacuo. The crude reaction mixture was then purified by column chromatography, giving the product (4 or 7).
9. All known compounds gave satisfactory data, all novel compounds were fully characterized by spectroscopic methods and HRMS.
10. K. A. Runcie and R. J. K. Taylor, Chem. Commun., 2002, 974.
11. 5 were synthesised according to a literature procedure: R. M. Moriaty, B. A. Berglund and R. Penmaster, Tetrahedron Lett., 1992, 33, 6065.