Simple and efficient stereocontrol of radical allylations of β-hydroxy esters

Tetrahedron Letters

Volumn 37, Issue 35, 1996, Pages 6335-6338

  Gerster, Michèle ^a   Audergon, Laurent ^a   Moufid, Nadira ^a   Renaud, Philippe ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ESTER DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030603079     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01396-2     Document Type: Article

References (25)

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4. c) Giese, B.; Bulliard, M.; Zeitz, H.-G. Synlett 1991, 425-427.
5. d) Giese, B.; Damm, W.; Wetterich, F.; Zeitz, H.-G. Tetrahedron Lett. 1992, 33, 1863-1866.
6. e) Giese, B.; Damm, W.; Wetterich, F.; Zeitz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885-5888.
7. (3) For a review on allylic strain in radical reactions, see: Giese, B.; Damm, W.; Batra, R. Chemtracts-Organic Chemistry, 1994, 335-370.
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9. (5) See ref. 2e and: a) Guindon, Y.; Yoakim, C.; Lemieux, R.; Boisvert, L.; Delorme, D.; Lavallée, J.-F. Tetrahedron Lett. 1990, 31, 2845-2848.
10. b) Guindon, Y.; Lavallée, J.-F.; Boisvert, L.; Chabot, C.; Delorme, D.; Yoakim, C.; Hall, D.; Lemieux, R.; Simoneau, B.; Tetrahedron Lett. 1991, 32, 27-30.
11. c) Durkin, F.; Liotta, D.; Rancourt, J.; Lavallée, J.-F.; Boisvert, L.; Guindon, Y. J. Am. Chem. Soc. 1992, 114, 4912-4914.
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24. (11) This can be attributed to the fact that chelation of the anti isomer generates in the most favorable conformation only one gauche interaction, the syn isomer generates two gauche interactions, see also ref. 6a.
25. (12) Tetrahydrofuran-2-yl substituted ester radicals behave similarly, see ref. 6b.