Highly asymmetric dihydroxylation of 1-aryl-1'-pyridyl alkenes

Tetrahedron Letters

Volumn 41, Issue 25, 2000, Pages 4865-4869

  Wang, Xin ^a   Zak, Mark ^a   Maddess, Mathew ^a   O'Shea, Paul ^a   Tillyer, Richard ^b   Grabowski, E J J ^b   Reider, Paul J ^b  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

1,1' diaryalkenes; Asymmetric dihydroxylation

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; HYDROXYLATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034686265     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00741-3     Document Type: Article

References (6)

1. Kolb, H. C. VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
2. Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993; pp. 227-272.
3. Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 448.
4. 1,1-Diaryl alkenes were prepared in a two step-reaction sequence as below. Attempts to prepare 1-phenyl-1′-substituted thienyl alkenes using this and other alternative methods were unsuccessful, due to the highly unstable nature of those targeted alkenes.
5. 2O exchangeable).
6. 13C NMR and HRMS), which are consistent with their assigned structures.