Substituent effects on the stereochemical course of electrophile- initiated tetrahydropyran-forming reactions: A possible stereoelectronic effect

Heterocycles

Volumn 52, Issue 3, 2000, Pages 1025-1028

  Hart, David J ^a   Patterson, Suzanne ^a   Zakarian, Alain ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 PENTEN 1,3 DIOL DERIVATIVE; METHYL GROUP; PHENYLSELENENYL CHLORIDE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0034161906     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-s119     Document Type: Article

References (13)

1. This paper is dedicated to Professor Teruaki Mukaiyama on the occasion of his 73rd birthday.
2. D. J. Hart, V. Leroy, G. H. Merriman, and D. G. J. Young, J. Org. Chem., 1992, 57, 5670.
3. D. J. Hart, G. H. Merriman, and D. G. J. Young, Tetrahedron, 1996, 52, 14437.
4. For other examples of tetrahydropyran synthesis via electrophile-initiated cycloetherification reactions see: I. Arai, T. D. Lee, R. Hanna, and G. D. Daves, Jr., Organometallics, 1982, 1, 742 and other articles cited in reference 2.
5. 3 and the corresponding cobalt-alkyne complexes, see: A. Zakarian, MS Thesis, The Ohio State University (1997).
6. Lactones (3) and (6) were prepared as described in reference 4 as follows: matrix equation presented
7. For an early reference on selenoetherification reactions see: K. C. Nicolaou and Z. Lysenko, Tetrahedron Lett., 1977, 1257.
8. Tetrahydropyrans (4) and (5) were separable. Compounds (7) and (8) were analyzed as a mixture.
9. H. B. Henbest and R. A. Wilson, J. Chem. Soc., 1957, 1958.
10. P. Chamberlain, M. L. Roberts, and G. H. Whitham, J. Chem. Soc. (B), 1970, 1374.
11. For a related observation involving a radical cyclization see: T. V. Rajanbabu, Acc. Chem. Res., 1991, 24, 139.
12. The aldehydes used in the table were prepared from the sodium salt of glutaconaldehyde: N. P. Lewis, P. W. McKen, and R. J. K. Taylor, Synlett, 1991, 898.
13. Tetrahydropyrans (13) and (14) were initally characterized as an inseparable mixture, but were further characterized by deprotection and separation of the resulting alcohols. Tetrahydropyrans (16) and (17) were separable. Tetrahydropyrans (19) and (20) were analyzed as a mixture.