Tetrahedron Letters p. 2393 - 2396 (1998)
Update date:2022-08-17
Topics:
Stratakis, Manolis
Vassilikogiannakis, Georgios
Orfanopoulos, Michael
The ene reaction of PTAD with the chiral allylic alcohol 4-methyl-3- penten-2-ol exhibits high threo diastereoselectivity in non polar solvents, whereas in polar solvents the diastereoselectivity decreases substantially. The results are discussed in terms of a steering effect between the hydroxyl and the incoming enophile during the formation of the diastereomeric syn and anti aziridinium imide intermediates.
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