Regioselective azide opening of 2,3-epoxy alcohols by [Ti(O-i-Pr)2(N3)2]: synthesis of .alpha.-amino acids

Chemistry, Biology, and Medicine of the Glycopeptide Antibiotics

“…Scheme 5. Synthesis of AA-4 derivative (R)-33 of vancomycin through enzymatic resolution according to Zhu et al [114] The catalytic asymmetric epoxidation (AE) of allylic alcohols, [115] the asymmetric dihydroxylation (AD) of olefins [116] and the asymmetric aminohydroxylation (AA) of olefins, [117] all developed by the Sharpless group, have been applied productively to the synthesis of aryl glycines as shown in Schemes 6, [118] 7, [119] and 8, [120] respectively. [119,120] The electrophilic amination of oxazolidinone derived enolates was developed by the Evans group in the late 1980s.…”

Small Rings by Azide Chemistry

“…An example of its use is the conversion of epoxyalcohol 65 into azidoalcohols 66 and 67 (Scheme 6.28 ). 93,94 Enantiopure aziridines can also be obtained from chiral 1,2 -diols. These are converted into cyclic sulfates 68 , 95 -97 or cyclic sulfi tes 69 .…”

Chemie, Biologie und medizinische Anwendungen der Glycopeptid-Antibiotika

“…Die katalytische asymmetrische Epoxidierung (AE) von Allylalkoholen, [115] die asymmetrische Dihydroxylierung (AD) von Olefinen [116] und die asymmetrische Aminohydroxylierung (AA) von Olefinen [117] ± Reaktionen, die von Sharpless et al entwickelt wurden ± wurden alle produktiv für die Synthese von Arylglycinen genutzt, wie in Schema 6 [118] , 7 [119] und 8 [120] [116] ).…”