High stereoselectivity in the Wittig reaction induced by the interaction of charges

Tetrahedron Letters

Volumn 37, Issue 24, 1996, Pages 4141-4144

  Klar, Ulrich ^a   Deicke, Peter ^a  

^a BAYER PHARMA AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

7 (3 BENZENESULFONAMIDOBICYCLO[2.2.1]HEPT 2 YL) 5 HEPTENOIC ACID; BICYCLO[3.3.0]OCTANE DERIVATIVE; CARBACYCLIN DERIVATIVE; DALTROBAN; PHOSPHORUS; PROSTACYCLIN DERIVATIVE; PROSTACYCLIN RECEPTOR; RAMATROBAN; REAGENT; SULFONAMIDE; THROMBOXANE RECEPTOR; THROMBOXANE RECEPTOR BLOCKING AGENT;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DRUG MIXTURE; DRUG POTENTIATION; DRUG SYNTHESIS; ISOMERISM; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY;

EID: 0029975541     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00780-0     Document Type: Article

References (12)

1. Aristoff P.A., Johnson P.D., Harrison A.W. J.Org.Chem. 1983, 48, 5341-5348.
2. Deicke P.; Klar U.; Vorbrüggen H. Biomed. Chem. Lett. 1992, 2, 439-444.
3. Lefer A.M. Drugs Future 1988, 13, 999-1005.
4. Ohtani M.; Matsuura T.; Watanabe F.; Narisada M. J.Org. Chem. 1991, 56, 2122-2127.
5. Perzborn E.; Boberg M.; Bühner K.; Böshagen, H.; Fiedler V.B.; Gardiner P.J.; Múller U.; Norman P.; Ritter W.; Rosentreter U.; Seuter F.; Weber H. Drugs Future 1991, 16, 701-705.
6. For a detailed description of the synthesis see WO 93/07,118 Schering AG.
7. To simplify the discussion, the carbacyclin numbering concerning the bicyclo[3.3.0]octane-skeleton will be maintained even for the truncated α-chain (n=0).
8. -1.
9. For an excellent discussion of the directing effects in the Wittig reaction see: Maryanoff B.E.; Reitz A.B.; Duhl-Emsweiler B.A. J. Am. Chem. Soc. 1985, 107, 217-226.
10. a) Krysan D.J.; Haight A.R.; Lallaman J.E.; Langridge D.C.; Menzia J.A.; Narayanan B.A.; Pariza R.J.; Reno D.S.; Rockway T.W.; Stuk T.L.; Tien J.H. Org. Prep. Proc. Int. 1993, 25, 437-443;
11. b) Takeuchi K.; Paschal J.W.; Loncharich R.J. J. Org. Chem. 1995, 60, 156-168;
12. Shing T.K.M.; Tsui H.-C.; Zhou Z.-H. J. Org. Chem. 1995, 60, 3121-3130.