Sulfoximines, epoxy

The a-halo sulfoximine (31) reacts with benzaldehyde and several ketones to afford epoxy sulfox-imines (equation 11 Table 4). 7 5 products (32a), (32b) and (32c) are each mixtures of two dia-stereomers due to the contiguous stereocenters at sulfur and the a-carbon atom. Product (32c) is a diastereomeric mixture in which the t-butyl and sulfoximino groups are predominantly (90%) cis. The epoxy sulfoximines (32) were viewed as potential intermediates in a homologation sequence for alde-... 

Uncatalyzed Additions of Nucleophilic Alkenes to C=X Table 4 Condensations of (31) with Caibonyl Compounds Giving Epoxy Sulfoximines ... 

Bromohydrins from epoxy sulfoximines. Chiral epoxides available from the unsaturated sulfoximines may be used as precursors of bromohydrins. Ring opening via the magnesium chelates affords a-bromoaldehydes, as a result of sulfinimine elimination. In the presence of BU4NBH4 the aldehydes are immediately reduced without much racemization. 

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