том 35 , издание 4 , страницы 451-454

Catalytic Asymmetric Aminohydroxylation (AA) of Olefins

Тип публикации: Journal Article

Дата публикации: 1996-03-01

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DOI: 10.1002/anie.199604511

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General Chemistry

Catalysis

Краткое описание

The stereospecific cis addition of “TsN” and H2O yields α-hydroxy-N-tosylamines (see below). This osmium-catalyzed process, which depends on Chloramine-T as the nitrenoid source, is rendered asymmetric in the presence of cinchona alkaloid ligands. The selectivities for reactions of the six olefins studied range from 33% ee (cis-stilbene) to 81% ee (trans-methylcinnamate). The active agent is presumably the compound Os(O)3NTs shown in square brackets. (DHQ)2-PHAL = bis(dihydro-quininyl)phthalazine (see preceding communication).

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