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14) catalyze such epoxidations with greater selectivity than for the corresponding cis-olefins under the same conditions. Here the mechanism is presumed to involve an electrophilic process, which is supported by the fact that only electron-rich alkenes are effectively epoxidized. In the case of trans-6-methyl-styrene (15), enantioselectivities of ca. 80% are observed [95TL7739]. ,," 16 Three-MemberedRing Systems 49 Another notoriously ill-behaved group of substrates are the terminal alkenes, which lack the steric definition necessary for most catalytic systems.

The organization is much the same as that of previous years. 2 EPOXIDES 3 . 2 . 1 Preparation of Epoxides Epoxides have been prepared by a variety of methods, but by far the most significant method is the epoxidation of olefins. The attractiveness of this approach lies in the ready availability of the necessary substrates, as well as an arsenal of well-characterized protocols for their epoxidation; the Sharpless epoxidation of allylic alcohols provides a classic example. Of course, of particular advantage in this methodology is the possibility to construct chiral epoxides.

Synthesis 1995, 307. Marzinzik, A. ; Rademacher, P. Synthesis 1995, 1131. ; NEdElec, J. Y. Synth. Commun. 1995, 25, 3529. -F. Synth. Commun. 1995, 25, 3549. Aitken, R. ; Bradbury, C. ; Morrison, J. J. Synlett 1995, 53. ; Viswajanani, R. Synlett 1995, 95. Feldman, K. S. Synlett 1995, 217. Fairbanks, A. ; Sinai, P. Synlett 1995, 277. Parsons, P. ; Penkett, C. ; Cramp, M. ; West, R. ; Saraiva, M. C. Synlett 1995, 507. ; Faure, R. Synlett 1995, 705. -F. Synlett 1995, 763. ; Wu, J. Synlen 1995, 850.

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