期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 69, 期 5, 页码 1704-1715出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo035745c
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The stereochemical course of the oxidation of chiral oxazolidinone-substituted enecarbamates has been studied for singlet oxygen (O-1(2)), dimethyldioxirane (DMD), and m-chloroperbenzoic acid (mCPBA) by examining of the special structural and stereoelectronic features of the enecarbamates. Valuable mechanistic insight into these selective oxidations is gained. Whereas the R-1 substituent on the chiral auxiliary is responsible for the steric shielding of the double bond and determines the sense of the T-facial diastereoselectivity, structural characteristic such as the Z/E configuration and the nature of the R-2 group on the double bond are responsible for the extent of the diastereoselectivity. Stereoelectronic steering by the vinylic nitrogen functionality controls the mode selectivity (ene reaction vs [2+2] cycloaddition) in the case of O-1(2).
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