Rhodium-catalyzed addition of arylboronic acids to 2-methylene-1,3-dithiane monoxide

Synlett

Volumn , Issue 10, 2007, Pages 1622-1624

  Yoshida, Suguru ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Addition; Arylboronic acid; Methylene dithiane monoxide; Rhodium

Indexed keywords

2 METHYLENE 1,3 DITHIANE MONOXIDE; BORONIC ACID DERIVATIVE; CARBENOID; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ADDITION REACTION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 34347335756     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-980373     Document Type: Article

References (19)

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11. (b) Addition to nitroalkenes: Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
12. 4 and concentrated in vacuo. Purification by chromatography on a silica gel column provided 2-benzyl-1,3-dithiane 1-oxide (3a, 65.6 mg, 0.29 mmol, 97%).
13. 13C NMR spectra of 3a were identical to the reported data: Page, P. C. B.; Wilkes, R. D.; Namwindwa, E. S.; Witty, M. J. Tetrahedron 1996, 52, 2125.
14. The mechanism for the stereoselective formation of the cis-product 3a is not clear at this stage. Protonation of the intermediate shown in Figure 1 would be the key step.
15. The relative stereochemistry of 5 is not clear.
16. We are tempted to assume the stereochemistry of 6b based on the plausible reaction mechanism shown here (Scheme 6). Attempts to prepare X-ray-quality crystals of 6b or related compounds are in progress. (Chemical Equation Presented)
17. Ogura, K.; Tsuchihashi, G. Tetrahedron Lett. 1971, 34, 3151.
18. The relative stereochemistry of 8 has not been determined.
19. Page, P. C. B.; Shuttleworth, S. J.; McKenzie, M. J.; Schilling, M. B.; Tapolczay, D. J. Synthesis 1995, 73.