5: Oxidation Reactions
- Page ID
- 168800
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)- 5.1: Oxidation of Alcohols
- Oxidation of alcohols to carbonyl compounds is a pivotal process in organic chemistry. In particular, the oxidations that use readily available molecular oxygen, especially ambient air, as the stoichiometric oxidant are the most preferable.
- 5.2: Epoxidation of Allylic Alcohols
- Epoxidation of allylic alcohols is a well developed practical process in asymmetric catalysis.
- 5.3: Epoxidation of Unfunctionalized Alkenes
- Asymmetric epoxidation of unfunctionalized alkenes affords an appealing strategy for the synthesis optically active organic compounds. This section covers some of the recent developments on this protocol.
- 5.4: Enantioselective Sulfoxidation
- Enantiopure sulfoxides serve as chiral auxiliary as well as intermediates for the synthesis of optically active compounds. Optically active sulfoxide structural unit is also present in many compounds that exhibit interesting biological properties. Development of methods for the asymmetric sulfoxidation has thus been active topic in asymmetric catalysis. This lecture covers the common methods that are used for the synthesis of optically active sulfoxides.
- 5.5: Baeyer-Villiger Oxidation (BVO)
- Insertion of oxygen atom in between the ketone carbonyl and an adjacent carbon yielding the expanded ester is called as Baeyer-Villiger oxidation (BVO). Under the influence of a chiral reagent, this oxidation can be carried out asymmetrically. In case of a racemic ketone, a chiral catalyst has the potential of performing a kinetic resolution. The catalytic asymmetric BVO remains as one of the most powerful methods to convert a ketone into an ester.
- 5.6: Dihydroxylation, Aminohydroxylation and Aziridination Reactions
- Insertion of oxygen atom in between the ketone carbonyl and an adjacent carbon yielding the expanded ester is called as Baeyer-Villiger oxidation (BVO). Under the influence of a chiral reagent, this oxidation can be carried out asymmetrically. In case of a racemic ketone, a chiral catalyst has the potential of performing a kinetic resolution. The catalytic asymmetric BVO remains as one of the most powerful methods to convert a ketone into an ester.