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Reactivity Umpolung-1 Ready Reactivity Umpolung: reversal of normal polarity electrophiles become nucleophiles nucleophiles become electrophiles Outline: 1. electrophilic heteroatoms 2. acyl anions 3. homoenolates 4. the cyclopropane tric…

Protecting Groups in Organic Synthesis-1 Ready Protecting groups are a sad fact of synthetic chemistry They are usually needed, but rarely desired Many syntheses have stalled because of trouble putting on or removing protecting groups 4 bas…

Oxidation of Unsaturated Systems 2 general reactivity patterns: X H X Yn+2 X+ Yn ++ OH simple example O A- Me2SCl+ S+ O + S + Cl- 2 electron oxidation 1 electron oxidation Xor -1 e- or X we will focus on oxidation of aromatic rings and enol/enolate systems Couple Eo Fe(III) + e- Fe(II…

1 Kinetic Resolutions Material outline: For the Scientist in you: Definitions Theoretical treatment For the technician in you: Practical considerations Useful KR’s Oxidative KR of allylic alcohols An extreme example Acylation/deacylation Hydrogenation olefins k…

Biomaterials 303 (2023) 122345 Available online 16 October 2023 0142-9612/© 2023 Published by Elsevier Ltd. Recent advances in nano- and micro-scale carrier systems for controlled delivery of vaccines Erika Yan Wang a,1, Morteza Sarmadi a,1, Binbin Ying a,b,c,1, Ana Jaklenec a,*, Robert Langer a…

Reagent/Reaction Use Ref Note DMSO/DCC (Pfitzner- Moffatt or Moffatt) Alcohol ketone/aldehyde Jacs 1963, 3027; Mech: JACS, 1965, 5561, JOC, 1967, 1926 First DMSO-based; DCC pain to remove; EDCI better DMSO/Ac2O “ Jacs 1967, 2416 DMSO/TFAA “ Jacs, 1975, 2758 DMSO/SO3-Pyridine (Parikh- D…

Reductions General Resource: Trost, Comp. Org. Syn. 1991, vol 8 March,1992, chap 19 Carey and Sundberg, vol B, Chap 5 Smith, Organic Synthesis, Chap 4 Material organized (roughly) by transformation From March, 1992, p1208 H H Two general classes: Transition metal hydrogenation and dissolvin…

1 R Co(CO)3(OC)3Co O O Δ (OC)3Co O R H O R H2 R H O (OC)4Co R (OC)4Co Co(CO)4 H H (CO)4CoH H2 CO R O H R CO (OC)3Co R (OC)3Co H R H2 R (OC)3Co R The Oxo process -developed in 1938 by Otto Roelen -Principle method for hydroformylation of terminal alkenes industrially …

Oxidations at Carbon General references March, Advanced Org Chem, 1992, 1158-1238 Trost, Comp. Org. Syn. 1991, vol 7 Carey and Sundberg, Advanced Org Chem, part B, 615-664 Smith, Org Syn, Chap 3 H CH3 C(-IV) R CH3 C(-III) R CH2 OH C(-1) R CH OH RR H2 C R C(-II) R C O R C(0) R CH O …

Epoxidation, Dihydroxylation, and the Utility of Epoxides and Diols Ready Outline: Epoxidation Condensation approaches Darzens condensation Sulfur ylides With organic peroxides Peroxy acids Peroxy iminic acids Dioxiranes DMDO Enantioselective versions Metal-catalyzed Approaches V(O)(acac)2 Sha…