Nickel catalyzed addition of organozincates to optically pure vinylic sulfoxides, synthesis of the phosphodiesterase IV inhibitor L-765,527 (CDP-840).

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7131-7134

  Houpis, Ioannis N ^a   Molina, Audrey ^a   Dorziotis, Ilias ^a   Reamer, Robert A ^a   Volante, R P ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

L 765527; PHOSPHODIESTERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030666813     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01766-8     Document Type: Article

References (26)

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16. For details on the general synthesis of chiral sulfoxides using 5, see ref 1a and 1b.
17. The amount of base was crucial. Excess reagent caused a shift of the equilibrium towards 6 and 7.
18. Indeed after this study was completed, an interesting report appeared where hindered vinyl sulfoxides were used for generation of vinyl Grignards in high yield: Satoh, T.; Tahano, K.; Someya, H.; Matsuda, K. Tetrahedron Lett. 1995, 36, 7097.
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25. 3ZnLi has been used in an ingenious way to effect catalytic cuprate additions to enones: Lipshutz, B.H.; Wood, M.R., Tirado R. J.Am. Chem.Soc. 1995, 117, 6126 and references therein.
26. The order of addition of the external ligand was not important. Inhibition was observed regardless if the ligand was added before or after the zincate.