Enantioselective allylation of β,γ-unsaturated aldehydes generated via Lewis acid induced rearrangement of 2-vinyloxiranes

Organic Letters

Volumn 4, Issue 1, 2002, Pages 83-86

  Lautens, Mark ^a   Maddess, Matthew L ^a   Sauer, Effiette L O ^a   Ouellet, Stéphane G ^a  

^a UNIVERSITY OF TORONTO   (Canada)

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EID: 0006170068     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016946a     Document Type: Article

References (23)

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12. For an alternative to the use of β,γ-unsaturated aldehydes, see: Hughes, G.; Lautens, M.; Wen, C. Org. Lett. 2000, 2, 107.
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18. Solution stored in a Wheaton bottle at -20°C to ensure consistency. It is highly recommended that the methanol be freshly distilled from magnesium and iodine.
19. This magnesium salt was obtained from drying the filtrate from the synthesis of 3 under high vacuum for 12 h.
20. The absolute configuration may be predicted from analogy with previous results. 3 is known to give si face attack while ent-3 provides the enantiomer. See: (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092;
21. (b) Vulpetti, A.; Gardner, M.; Gennari, C.; Bernardi, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1993, 58, 1711.
22. Sadhu, K. M.; Matteson, D. S. Tetrahedron Lett. 1986, 27, 795.
23. 3N, EtOAc/Hex).