0: Readings
- Page ID
- 23321
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)All of the reading assignments from journals can be found here.
Week 1
- Misassigned Structures: Angew. Chem. Int. Ed., 2005, 44, 1012-1044.
- History of ChemDraw: Angew. Chem. Int. Ed., 2014, 53, 11140-11145.
- Diversity Oriented Synthesis: Angew. Chem. Int. Ed., 2004, 43, 46-58.
- Green Chemistry: Acc. Chem. Res., 2002, 35, 686-694.
- Redox Economy: Angew. Chem. Int. Ed., 2009, 48, 2854-2867.
- Ideal Synthesis: J. Org. Chem., 2010, 75, 4657-4673.
- Scalable Synthesis: Nat. Prod. Rep., 2014, 31, 419-432.
- Umpolung Chemistry: Angew. Chem. Int. Ed., 1979, 18, 239-336.
- Chiral Pool Retrosynthesis - Quinic Acid: Tetrahedron Lett., 1986, 27, 5071-5074.
- Zaragosic Acid C: J. Am. Chem. Soc., 2008, 130, 17281-17283.
- Asymmetric Ammonia Synthon: J. Org. Chem., 1986, 51, 2820-2822.; J. Org. Chem., 1992, 57, 2114-2121.
- Oxidative Kinetic Resolution Example: Angew. Chem. Int. Ed., 2008, 47, 3755-3758.
Quinine
- Stork's Synthesis: J. Am. Chem. Soc., 2001, 123, 3239-3242.
- Historical Overview: Angew. Chem. Int. Ed., 2007, 46, 1378-1413.
- Proof of Woodward's Formal Synthesis: Angew. Chem. Int. Ed., 2008, 47, 1736-1740.
Week 2
- A(1,3)-Strain Review: Chem. Rev., 1989, 89, 1841-1860.
- Substrate Directed Reactions Review: Chem. Rev., 1993, 93, 1307-1370.
- Fürst-Plattner Example 1: Tetrahedron Lett., 1998, 39, 6811-6814.
- Fürst-Plattner Example 2: J. Chem. Soc., Perkin Trans. 2, 1978, 627-632.
- Fürst-Plattner Example 3: J. Am. Chem. Soc., 1983, 105, 2354–2358.
- Fürst-Plattner Electronic Exceptions: J. Am. Chem. Soc., 2000, 122, 168–169.
- Dermostatin A: Angew. Chem. Int. Ed., 2001, 40, 3224-3227.
Week 3
- Protecting Groups Review: Angew. Chem. Int. Ed. Engl., 1996, 35, 2056-2083.
Week 4
Organometallic Reagents
- Grignard Reagents in Synthesis: Angew. Chem. Int. Ed., 2003, 42, 4302-4320.
- Lithium Reagent Review: Acc. Chem. Res., 1996, 29, 552-560.
- Lithioamine equivalents: J. Org. Chem., 1990, 55, 2578-2580.
- Seminal Cerium Chloride Paper: J. Am. Chem. Soc., 1989, 111, 4392-4398.
- Cerium Reagents: J. Org. Chem., 1984, 49, 3904-3912.
- 2-Oxazoline Synthesis: Angew. Chem. Int. Ed. Engl., 1976, 15, 270-281.
- Oxazoline Metalation: J. Org. Chem., 1975, 40, 3158-3159.
Weinreb Amides
- Original Publication: Tetrahedron Lett. 1981, 39, 3815-3818.
- Review: J. Prakt. Chem., 1997, 339, 517-524.
- Review: Synthesis, 2008, 3707-3738.
- Formation: J. Org. Chem., 2004, 69, 8984-8986.
- Formation: Tetrahedron Lett., 1995, 36, 5461-5464.
Higher Order Cuprates
- Where is the Cyano Ligand?: J. Org. Chem., 1994, 59, 7578-7587.
- On Lithium!: Chem. Commun., 1996, 815-816.
Week 5
- Chelate Review: Acc. Chem. Res., 1993, 26, 462-468.
- Cram's Rule: J. Am. Chem. Soc., 1952, 74, 5828-5835.
- Cram Chelate: J. Am. Chem. Soc., 1959, 81, 2748-2755.
- Keck's Lewis Acid study: Tetrahedron Lett., 1984, 25, 265-268.
Week 6
- Redox Economy: Angew. Chem. Int. Ed., 2009, 48, 2854-2867.
- Asymmetric Borane Reductions: Acc. Chem. Res., 1992, 25, 16-24.
- Modified Wolff-Kishner: J. Am. Chem. Soc., 2004, 126, 5436-5445.
- Luche Reduction: J. Am. Chem. Soc., 1981, 103, 5454-5459.
- Stryker Reduction: J. Am. Chem. Soc., 1988, 110, 291-293.
- Directed Borohydride: J. Am. Chem. Soc., 1988, 110, 3560-3578.
- Stereochemical Models of Reduction: J. Org. Chem., 1984, 49, 778-788.
- Organoborane Reductions: J. Org. Chem., 1988, 53, 2916-2920.
- CBS reagent prep: J. Org. Chem., 1993, 58, 2880-2888.
- CBS Transition State: Tetrahedron Lett., 2009, 50, 1324-1327.
- Chemoselective Aldehyde Reduction: Tetrahedron Lett., 1983, 24, 4287-4290.
- Alkoxydialkylborane reductions: Tetrahedron Lett., 1987, 28, 155-158.
- Chelate Control: Tetrahedron Lett., 1985, 26, 5139-5142.
Tar-BH
- Enantioselective Reductions with Boronic Esters: Tetrahedron Lett., 2007, 48, 9025-9029.
- Boronic Ester 2: Synthesis, 2008, 23, 3874-3876.
- Boronic Ester 3: Org. Lett., 2009, 11, 4358-4361.
Week 7
- IBX Prep: J. Org. Chem., 1999, 64, 4537-4538.
- IBX oxidation procedure: Org. Lett., 2002, 4, 3001-3003.
- NHC catalyzed oxidation of allylic or benzylic alcohols to esters: Org. Lett., 2007, 9, 371-374.
- NHC catalyzed oxidation of aldehydes to esters: Org. Lett., 2008, 10, 4331-4334.
- Fetizon's reagent: J. Chem. Soc. D, 1969, 1102-1102.
Tempo
- With Cupric Ions and Oxygen: J. Am. Chem. Soc., 1984, 106, 3374-3376.
- Primary Selective: Org. Lett., 2001, 3, 3041-3043.
- Use in Total Synthesis: Org. Lett., 2004, 6, 3985-3988.
- Review: Synthesis, 1996, 10, 1153-1176.
- Synthesis of alpha-hetereoatom substituted aldehydes: Tetrahedron Lett. ,1992, 33, 5029-5032.
Week 8
- Cyclohexanone alkylation example: Org. Lett., 2007, 9, 2839-2842.
- Elemanolides: Tetrahedron, 1988, 44, 1369-1392.
- beta-vetivone synthesis: J. Am. Chem. Soc., 1973, 95, 3414-3415.
- Evans Auxiliary: J. Am. Chem. Soc., 1982, 104, 1737-1739.
Myers Auxiliary
Week 9
- Review: Chem. Soc. Rev., 2004, 33, 65-75.
- Boron Enolates: Chem. Letters, 1976, 5, 559-562.
- Boron Enolates 2: J. Am. Chem. Soc., 1979, 101, 6120-6123.
- Controlling Enolate Geometry: J. Am. Chem. Soc., 1989, 111, 3441-3442.
- E-selective enolate formation: J. Am. Chem. Soc., 1991, 113, 9571-9574.
- Evans Asymmetric Alkylation: J. Am. Chem. Soc., 1982, 104, 1737-1739.
- Evans Asymmetric Aldol Reaction: J. Am. Chem. Soc., 1981, 103, 2127-2129.
- Crimmins Auxilliary "Anti-Evans" product: J. Org. Chem., 2001, 66, 894-902.
- Magnesium catalyzed anti-Aldol: J. Am. Chem. Soc., 2002, 124, 392-393.
- Anti-selective Boron Aldol: J. Am. Chem. Soc., 1997, 119, 2586-2587.
- Ghosh anti-Aldol: J. Am. Chem. Soc., 1996, 118, 2527-2528.
- Prelog-Djerassi Lactone Synthesis: Tetrahedron Lett., 1982, 23, 807-810.
Acetate Aldol
- Sammakia Auxiliary: Org. Lett., 2004, 6, 23-25.
- Sammakia Auxiliary 2: J. Org. Chem., 2006, 71, 6262-6265.
- Sammakia Auxiliary 3: Org. Lett., 2004, 6, 3139-3141.
- Crimmins Auxiliary: Org. Lett., 2007, 9, 149-152.
- Olivio Auxiliary: Tetrahedron, 2004, 60, 9397-9403.
Mukaiyama Aldol
- Yamamoto Lewis-acid catalyst: J. Am. Chem. Soc., 1991, 113, 1041-1042.
- Carreira Lews-acid catalyst: J. Am. Chem. Soc., 1994, 116, 8837-8838.
Week 10
Diels-Alder
- Diels-Alder in Total Synthesis: Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
- Intramolecular DA: Angew. Chem., Int. Ed. 2001, 40, 820-849.
- Intramolecular DA: Synthesis 2002, 2457-2463.
- Catalytic Enantioselective DA: Angew. Chem., Int. Ed. 2002, 41, 1650-1667.
- Asymmetric DA: J. Am. Chem. Soc. 1988, 110, 1238-1256.
- Asymmetric DA: J. Am. Chem. Soc. 1984, 106, 4261-4263.
- Diastereoselectivity of DA: Angew. Chem., Int. Ed. 1987, 26, 1184-1186.
- Chiral Catalyst DA: J. Am. Chem. Soc. 1993, 115, 6460-6461.
- Chiral Organocatalyst DA: J. Am. Chem. Soc. 2000, 122, 4243-4244.
- Pumiliotoxin C: Tetrahedron Lett. 1977, 18, 1253-1256.
- Pumiliotoxin C: J. Am. Chem. Soc. 1978, 100, 5179-5185.
- Estrone: J. Am. Chem. Soc. 1980, 102, 5253-5261.