Vicinal halohydrins are useful synthetic intermediates in the synthesis of marine natural products, such as chlorosulfolipids. Here, we report the results of our investigations that led to the development of the mild method for the practical stereocontrolled synthesis of vicinal halohydrins and haloamines from unsaturated three-member ring heterocycles.<br/>The reaction of vinyl epoxyesters with commercial boron halide solutions was investigated. The corresponding vicinal chlorohydrins and bromohydrins were obtained in high yields with high regioselectivities and exclusive diastereoselectivity, in short times, after simple work-up. The opening of the vinyl aziridines was also successfully realized to afford regioselectively the corresponding haloamines.<sup>2</sup><br/>We will also present the results of our studies on the synthesis of the corresponding vicinal fluorohydrins from vinyl epoxides.

Practical stereocontrolled synthesis of vicinal halohydrins and haloamines from vinyl epoxides and vinyl aziridines

253rd National Meeting (2017)

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