Gallium-mediated allyl transfer from bulky homoallylic alcohol to aldehydes via retro-allylation: Stereoselective synthesis of both erythro- and threo-homoallylic alcohols

Organic Letters

Volumn 7, Issue 16, 2005, Pages 3577-3579

  Hayashi, Sayuri ^a   Hirano, Koji ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

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Indexed keywords

EID: 23944526293     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0515199     Document Type: Article

References (27)

1. Throughout this manuscript, we have adopted the unambiguous erythrolthreo nomenclature proposed by Noyori: Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106-2108.
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11. Retro-allylations from lithium, magnesium, and zinc alkoxides were observed. Among them, Knochel reported threo selectivity, (a) Benkeser, R. A.; Siklosi, M. P.; Mozdzen, E. C. J. Am. Chem. Soc. 1978, 100, 2134-2139.
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13. (c) Jones, P.; Knochel, P. J. Org. Chem. 1999, 64, 186-195. We have serendipitously found similar behavior of zirconium homoallylic alkoxides. See ref 3c.
14. Under harsh conditions, retro-allylation took place by the action of tin: (d) Peruzzo, V.; Tagliavini, G. J. Organomet. Chem. 1978, 162, 37-44.
15. (e) Giesen, V. Dissertation, University Marburg, Germany, 1989.
16. Ruthenium-catalyzed deallylation was reported: (f) Kondo, T.; Kodoi, K.; Nishinaga, E.; Okada, T.; Morisaki, Y.; Watanabe, Y.; Mitsudo, T. J. Am. Chem. Soc. 1998, 120, 5587-5588.
17. For convenience, throughout the manuscript, crotylation, methallylation, and prenylation are defined as introductions of 1-methyl-2-propenyl, 2-methyl-2-propenyl, and 1,1-dimethyl-2-propenyl groups, respectively, into a carbonyl group. On the other hand, crotyl, methallyl, and prenyl groups denote herein 2-butenyl, 2-methyl-2-propenyl, and 3-methyl-2-butenyl groups, respectively.
18. Representative examples: (a) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609-6610.
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27. Relative configuration of erythro-1f was determined by X-ray crystallographic analysis after derivatization. See Supporting Information.