Asymmetric syn‐Dihydroxylation of β‐Substituted (2R)‐N‐(α,β‐Enoyl)bornane‐10,2‐sultams

Variously β‐substituted (2 R )‐ N ‐[( E )‐α,β‐enoyl]bornane‐10,2‐sultams were oxidized with OsO 4 /4‐methylmorpholine 4‐oxide in a highly stereoselective manner. In all cases, the attack occurred on the C(α)‐ re face. The absolute configurations of all products were determined by chemical correlation. Mechanistic considerations about the reactive conformation as well as fully refined X‐ray crystal structures of the dihydroxylated products are discussed. New neutral conditions for sultam acylation, applicable to the preparation of the taxol and Taxotere ® C(13) side chain as well as of Cardizem ® and chloramphenicol precursors, are also presented.