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Harold C. Simmons Comprehensive Cancer Center Bioinformatics Data Science Shared Resource Data Science On-Demand User Agreement SCCC-DSSR This agreement is between the DSSR client named below and the Director of SCCC-DSSR, Professor Jeon Lee. By signing this document, user acknowledges and agrees to the conditions listed below. DSSR client (Full Name

Jeffrey SoRelle, M.D., Assistant Instructor of Pathology studies the mechanisms of allergy at a genetic level.

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 Sharpless AE Metal Oxo’s MTO Fe, Pt and Mn-based (Salen)Mn Jacobsen AE Epoxide Ring Opening Opening under acid or basic conditions Organocopper additions Reactions of epoxy alcohols Dihydroxylation

Publications for Thomas Carroll, Ph.D.

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 trick 5. sulfone chemistry Normal reactivity: X x = heteroatom d = donor (Nu-) a = acceptor (E+) d a d a d X X X X or 1 3 1 5 How to make: X X or X X 1 2 1 4 complimentary

Li (Xiaochun) Lab publications

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- Doering) “ JACS, 1967, 5505 Often under ambient conditions; best for α-chiral aldehydes/ketones (COCl)2/DMSO (swern) “ JOC, 1978, 2480; mech: Tet. 1978, 1651 Most commonly used; DMSO/Ac2O

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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 C(+I) H CH2 OH C(-II) H CH O C(0) C(II) R COR O C(+III) H COH O C(+II) O C O C(+IV) RO COR O C(+IV) alkane RCH2M RCH2SiR3 RCH2X X=halide RCH2NR2 RCH2SR RCH2PR2 Acetal: RCH(OR)2

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