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Gandon, V.; Thorimbert, S.; Malacria, M., Science of Synthesis, (2009) 46, 218.
Chiral allenes are versatile intermediates for asymmetric syntheses via axial-to-centered chirality transfer.[146] Their use in the preparation of 1,3-dienes and especially exocyclic cycloalkenes has been reported; thus, treatment of a 1,2-dien-6-ynes with a slight excess of titanium(IV) isopropoxide and isopropylmagnesium chloride affords titanabicyclopentenes that can be reacted further with various aldehydes or imines to furnish functionalized E,E-exocyclic dienes. One such conversion, using the chiral allene 157 as the starting material, gives the diene 158 with complete conservation of stereochemistry (Scheme 55).[147]
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References
[146] | Me, M., Meee. Mee., (8888) 888, 8888. |
[147] | Meeee, M.; Meeeee, M.; Meeeeee, M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 88888. |
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- 8.Meeeee-Meee, (8888) 8/8e, 88.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 88.