Aminohydroxy lation

In a related contribution O Brien described the AA on styrenes and converted the amino alcohols into enantiopure diamines by using a reaction strategy similar to Janda s [83], Further synthetic applications of the AA include a new access to Evans chiral oxazolidinones [84], the enantioselective synthesis of a-amino ketones from silyl enol ethers [85], the stereoselective synthesis of cyclohexyl norstatine [86], and a route towards amino cyclitols by aminohydroxy-lation of dienylsilanes [87]. 

Application of the AA [103] resulted in an even shorter synthesis of 88. The aminohydroxy-lation was carried out with a slightly higher catalyst loading [1 mol % of Os, 2.5 mol % of (DHQ)2PHAL] compared with the dihydroxylation sequence and furnished tosyl protected phenylisoserine ester 87 with 82% ee in 69% yield. The enantiomeric excess of 87 was further raised to 92% ee by trituration with ethyl acetate. Deprotection and conversion into benzamide 88 afforded the C-13 side chain in a total of three steps. 

Side Note 17.3. c/s-v/c-Aminohydroxy-lation of C=C Double Bonds... 

Aryl 2-alkenoates show a reversed regioselectvity in the asymmetric aminohydroxy-lation. ... 

---