A potential ambiguity in the stereochemical description of complex paracyclophanes

Tetrahedron Asymmetry

Volumn 9, Issue 4, 1998, Pages 539-541

  Pye, P J ^a   Rossen, K ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PARACYCLOPHANE DERIVATIVE;

ARTICLE; GEOMETRY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032570489     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00041-X     Document Type: Article

References (10)

1. (a) Cahn, R. S.; Ingold, C. K.; Prelog, V. Experimentia 1956, 12, 81.
2. (b) Cahn, R. S.; Ingold, C. K.; Prelog, V. Angew. Chem. Int. Ed. Engl. 1966, 5, 385.
3. (c) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds, Wiley, New York, 1994.
4. (a) Prelog, V.; Helmchen, G. Angew. Chem. Int. Ed. Engl. 1982, 21, 567.
5. (b) Helmchen, G. In Methods of Organic Synthesis (Houben-Weyl), Stereoselective Synthesis (Ed. G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme Verlag, Stuttgart, 1996, Chapter 1.
6. Mata, P.; Lobo, A. M.; Marshall, C.; Johnson, A. P. Tetrahedron: Asymmetry 1993, 4, 657.
7. (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207.
8. (b) Rossen, K.; Pye, P. J.; Maliakal, A.; Volante, R. P. J. Org. Chem. 1997, 62, 6462.
9. 2 group.
10. 1 does not lead to a change in stereochemical descriptor. Although compound 1 can be unambiguously assigned as S-, it may be helpful to designate the pilot atom thus arriving at the chiral descriptor 4S-. The Cram convention is the more commonly used numbering system.