Asymmetric [2,3]-wittig rearrangement induced by a chiral carbanion whose chirality was transferred from an epoxide

Organic Letters

Volumn 7, Issue 26, 2005, Pages 5913-5915

  Sasaki, Michiko ^a   Higashi, Mariko ^a   Masu, Hyuma ^b   Yamaguchi, Kentaro ^b   Takeda, Kei ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 30144434126     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052544h     Document Type: Article

References (31)

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26. 2 resulted in the formation of (Z)-5 in 21% yield and 37% ee, which will be reported elsewhere. Kawanishi, E.; Takeda, K. Hiroshima University, Japan. Unpublished results.
27. For the preparation of 8a,b and determination of their absolute stereochemistries, see the Supporting Information.
28. To the best of our knowledge, the solvent has not been used in [2,3]-Wittig rearrangement, probably because the rate of racemization of the carbanion has been thought to be much faster than that of the reaction with an electrophile at temperatures higher than its freezing point (11°C).
29. (S)-11 was prepared from the corresponding allyl alcohol according to the kinetic resolution procedure of Sharpless (see ref 11). On the basis of the results for [2,3]-Wittig rearrangement of (S)-12 (Table 3), we deduced that [2,3]-Wittig rearrangement of (S)-11 proceeds with inversion of configuration at the lithium-bearing carbon atom in the same way as reported for the alkyl counterparts (see ref 2).
30. 2. Gao, Y.; Klunder, J. M.; Hanson, R. M.; Masamune, H.; Ko, S. Y.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
31. The absolute configuration of the major enantiomer was determined to be R by comparison of the chiral HPLC to the one derived from (R)-mandelic acid (see Supporting Information), indicating an inversion of configuration at the lithium-bearing carbon atom (according to the protocol of Sharpless, see ref 11).