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Kinetic resolution under Sharpless epoxidation

Scheme 8.8. Reactions of a chiral allylic alcohol under Sharpless epoxidation conditions (Ti(0-i-Pr)4, /-BuOOH) using the chiral tartrates given (DIPT = diisopropyltartrate). (a) The matched case, in which the preferred approach of the asymmetric catalyst and the diastereoselectivity of the substrate are the same, (b) The mismatched case, (cj An example of a Sharpless kinetic resolution (KR). Scheme 8.8. Reactions of a chiral allylic alcohol under Sharpless epoxidation conditions (Ti(0-i-Pr)4, /-BuOOH) using the chiral tartrates given (DIPT = diisopropyltartrate). (a) The matched case, in which the preferred approach of the asymmetric catalyst and the diastereoselectivity of the substrate are the same, (b) The mismatched case, (cj An example of a Sharpless kinetic resolution (KR).
Certain vinylstannanes will undergo cyclopropanation with diiodomethane and samarium amalgam.69 71 Epoxidation of the double bond can be carried out with meta-chloroperoxybenzoic acid,71,72 and the kinetic resolution of a 3-stannylallyl alcohol has been achieved under Sharpless conditions (equation 8-38)73... [Pg.122]


See other pages where Kinetic resolution under Sharpless epoxidation is mentioned: [Pg.205]    [Pg.205]    [Pg.205]    [Pg.205]    [Pg.125]    [Pg.646]    [Pg.217]    [Pg.1071]    [Pg.1072]   


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