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N ‐Halocarbamate Salts Lead to More Efficient Catalytic Asymmetric Aminohydroxylation

1996; Wiley; Volume: 35; Issue: 23-24 Linguagem: Inglês

10.1002/anie.199628131

1521-3773

Guigen Li, Hubert Angert, K. Barry Sharpless,

Synthetic Organic Chemistry Methods

Better enantioselectivities and convenient deprotection make the sodium salts of N-chlorocarbamates the oxidant/nitrogen source of choice for the osmium/cinchona alkaloid catalyzed asymmetric aminohydroxylation (AA) of olefins [e.g. Eq. (a)]. This methodology simplifies the synthesis of a vast array of compounds such as unnatural amino acids and other pharmacologically important compounds. DHQH = dihydroquinine, PHAL = 1,3-phthalazinediyl, Z = benzyloxycarbonyl.