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The Simplifying Synthesis Ultimate Guide To Conformational Analysis
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A chemistry lecture on the conformational analysis of organic compounds.
Timestamps:
Newman projections, nomenclature 0:42
Alkane Conformation 1:42
Allylic Strain 7:10
Cyclic Systems 11:14
Cyclohexane Substituent Effects: Heterocycles, Anomeric Effect 13.39
Fused Ring Systems: Conformational Transmission, Regiochemistry of Enolate formation 16:48
Conformational Analysis in Synthesis: Felkin-Ahn Model, Chelation Control, Cyclohexanone Reduction, Case Studies 20:55
Conformational Effects in Carbohydrate Chemistry: Superarmed/disarmed Donors 26:33
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Socials:
References:
Stereochemistry of Organic Compounds, E. L. Eliel, L. Ernest, S. H. Wilen, L. N. Mander. Wiley, 1994.
Angew. Chem. Int. Ed. 2000, 39, 2054-2070 (Conformation Design of Open‐Chain Compounds)
Angew. Chemie 2020, 132, 14302–14314 (Conformational Design Principles in Total Synthesis)
CH206/215 Lecture notes, Prof D. Evans and Prof A. Myers
Chem. Sci., 2015, 6, 3565 (Can acyclic conformational control be achieved via a sulfur–fluorine gauche effect?)
Nat Prod Rep. 2015;32(8):1183-1206 (Conformation-Activity Relationships of Polyketide Natural Products)
Chem. Rev. 1989, 89, 8, 1841–1860 (Allylic 1-3-Strain as a Controlling Element in Stereoselective Transformations)
J. Am. Chem. Soc., Vol. 107, No. 18, 1985 (Barriers to rotation adjacent to double bonds)
Steric and Stereoelectronic Effects in Organic Chemistry. Springer, 2016
J. Org. Chem. 1978, 43, 2705 (Synthesis of 2,6-diacetonylpiperidine. X-ray diffraction analysis of its N-benzoyl derivative)
Pure & Appi. Chem., Vol.53, pp.11O9—1127 (Chiral Enolate Design)
Chem. Sci., 2020, 11, 10928 (Total Synthesis of Dimeric Securinega Alkaloids (-)-Flueggenines D and I)
Chemistry Open 2019,8, 788–806 (A Benchmark of Density Functional Approximations For Thermochemistry and Kinetics of Hydride Reductions of Cyclohexanones)
J. AM. CHEM. SOC. 2010,132, 4399–4408 (Overriding Felkin Control: A General Method for Highly Diastereoselective Chelation-Controlled Additions to Silyloxy Aldehydes)
J. Am. Chem. Soc. 2020, 142, 8116−8121 (Asymmetric Total Synthesis of (−)-Spirochensilide A)
Tet Lett. 1984,25,42,4775-4778 (Highly stereoselective reduction of α-methylthio and α-phenylthio ketones synthesis of syn- and anti-β-methylthio- and β-phenylthioalcohols)
Chem. - A Eur. J. 2001, 7, 2075–2088.(Molecular Signal Transduction by Conformational Transmission: Use of Tetrasubstituted Perhydroanthracenes as Transducers)
ChemPhysChem 2021, 22, 641 –648 (The Gauche Effect in XCH2CH2X Revisited)
J. Am. Chem. Soc. 1991, 113, 4, 1434–1435 (Torsional effects in glycoside reactivity: saccharide couplings mediated by acetal protecting groups)
J. Am. Chem. Soc. 2007, 129, 29, 9222–9235 (“Super Armed” Glycosyl Donors: Conformational Arming of Thioglycosides by Silylation)
Sel. Glycosylation Synth. Methods Catal., Wiley-VCH Verlag, 2017, pp. 29–58 (Application of Armed, Disarmed, Superarmed, and Superdisarmed Building Blocks in Stereocontrolled Glycosylation and Expeditious Oligosaccharide Synthesis)
Timestamps:
Newman projections, nomenclature 0:42
Alkane Conformation 1:42
Allylic Strain 7:10
Cyclic Systems 11:14
Cyclohexane Substituent Effects: Heterocycles, Anomeric Effect 13.39
Fused Ring Systems: Conformational Transmission, Regiochemistry of Enolate formation 16:48
Conformational Analysis in Synthesis: Felkin-Ahn Model, Chelation Control, Cyclohexanone Reduction, Case Studies 20:55
Conformational Effects in Carbohydrate Chemistry: Superarmed/disarmed Donors 26:33
SUPPORT THE CHANNEL ON PATREON:
Socials:
References:
Stereochemistry of Organic Compounds, E. L. Eliel, L. Ernest, S. H. Wilen, L. N. Mander. Wiley, 1994.
Angew. Chem. Int. Ed. 2000, 39, 2054-2070 (Conformation Design of Open‐Chain Compounds)
Angew. Chemie 2020, 132, 14302–14314 (Conformational Design Principles in Total Synthesis)
CH206/215 Lecture notes, Prof D. Evans and Prof A. Myers
Chem. Sci., 2015, 6, 3565 (Can acyclic conformational control be achieved via a sulfur–fluorine gauche effect?)
Nat Prod Rep. 2015;32(8):1183-1206 (Conformation-Activity Relationships of Polyketide Natural Products)
Chem. Rev. 1989, 89, 8, 1841–1860 (Allylic 1-3-Strain as a Controlling Element in Stereoselective Transformations)
J. Am. Chem. Soc., Vol. 107, No. 18, 1985 (Barriers to rotation adjacent to double bonds)
Steric and Stereoelectronic Effects in Organic Chemistry. Springer, 2016
J. Org. Chem. 1978, 43, 2705 (Synthesis of 2,6-diacetonylpiperidine. X-ray diffraction analysis of its N-benzoyl derivative)
Pure & Appi. Chem., Vol.53, pp.11O9—1127 (Chiral Enolate Design)
Chem. Sci., 2020, 11, 10928 (Total Synthesis of Dimeric Securinega Alkaloids (-)-Flueggenines D and I)
Chemistry Open 2019,8, 788–806 (A Benchmark of Density Functional Approximations For Thermochemistry and Kinetics of Hydride Reductions of Cyclohexanones)
J. AM. CHEM. SOC. 2010,132, 4399–4408 (Overriding Felkin Control: A General Method for Highly Diastereoselective Chelation-Controlled Additions to Silyloxy Aldehydes)
J. Am. Chem. Soc. 2020, 142, 8116−8121 (Asymmetric Total Synthesis of (−)-Spirochensilide A)
Tet Lett. 1984,25,42,4775-4778 (Highly stereoselective reduction of α-methylthio and α-phenylthio ketones synthesis of syn- and anti-β-methylthio- and β-phenylthioalcohols)
Chem. - A Eur. J. 2001, 7, 2075–2088.(Molecular Signal Transduction by Conformational Transmission: Use of Tetrasubstituted Perhydroanthracenes as Transducers)
ChemPhysChem 2021, 22, 641 –648 (The Gauche Effect in XCH2CH2X Revisited)
J. Am. Chem. Soc. 1991, 113, 4, 1434–1435 (Torsional effects in glycoside reactivity: saccharide couplings mediated by acetal protecting groups)
J. Am. Chem. Soc. 2007, 129, 29, 9222–9235 (“Super Armed” Glycosyl Donors: Conformational Arming of Thioglycosides by Silylation)
Sel. Glycosylation Synth. Methods Catal., Wiley-VCH Verlag, 2017, pp. 29–58 (Application of Armed, Disarmed, Superarmed, and Superdisarmed Building Blocks in Stereocontrolled Glycosylation and Expeditious Oligosaccharide Synthesis)
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