1. The diastereoselective transformation proceeds via coordination of the Dy(OTf)3 catalyst to the carbonyl and amine groups, forming a 6-membered ring transition state that rigidly positions the substituents to give a single diastereomer.
2. The transformation involves a 1,3-dipolar cycloaddition of the azide with the alkyne, followed by rhodium-catalyzed hydration of the resulting triazole to form the alcohol.
3. The transformation proceeds via a palladium-catalyzed coupling of the iodoarene with the alkene, followed by deprotection and oxidation to form the natural product Dalescon
1. The diastereoselective transformation proceeds via coordination of the Dy(OTf)3 catalyst to the carbonyl and amine groups, forming a 6-membered ring transition state that rigidly positions the substituents to give a single diastereomer.
2. The transformation involves a 1,3-dipolar cycloaddition of the azide with the alkyne, followed by rhodium-catalyzed hydration of the resulting triazole to form the alcohol.
3. The transformation proceeds via a palladium-catalyzed coupling of the iodoarene with the alkene, followed by deprotection and oxidation to form the natural product Dalescon
1. The diastereoselective transformation proceeds via coordination of the Dy(OTf)3 catalyst to the carbonyl and amine groups, forming a 6-membered ring transition state that rigidly positions the substituents to give a single diastereomer.
2. The transformation involves a 1,3-dipolar cycloaddition of the azide with the alkyne, followed by rhodium-catalyzed hydration of the resulting triazole to form the alcohol.
3. The transformation proceeds via a palladium-catalyzed coupling of the iodoarene with the alkene, followed by deprotection and oxidation to form the natural product Dalescon
1. The diastereoselective transformation proceeds via coordination of the Dy(OTf)3 catalyst to the carbonyl and amine groups, forming a 6-membered ring transition state that rigidly positions the substituents to give a single diastereomer.
2. The transformation involves a 1,3-dipolar cycloaddition of the azide with the alkyne, followed by rhodium-catalyzed hydration of the resulting triazole to form the alcohol.
3. The transformation proceeds via a palladium-catalyzed coupling of the iodoarene with the alkene, followed by deprotection and oxidation to form the natural product Dalescon
1. Please provide a plausible mechanism for the following transformation, explaining the complete diastereoselectivity obtained. (Org. Lett.
2020, 22, 21, 8555)
HO NH2 HN O Dy(OTf)3 + DCE, 90 °C O N Me N Me
70% yield
2. Please provide a plausible mechanism for the following transformation. (Org. Lett. 2021, 23, 20, 7771–7775)
OTMS 1) TsN3, CuTc, PhMe
CHO 2) Rh2(OCt)4 (2 mol%), PhMe, 90 °C OTMS then Al2O3 OTMS O TMSO
CHO
64% yield
3. Please provide a plausible mechanism for the following transformation. (J. Am. Chem. Soc. 2021, 143, 21270−21274)
OH NHBoc PdCl2, P(4-F-C6H4)3 O O O NBE, Cs2CO3, MeCN then HCl, Fe2(SO4)3 O O + O I (4 steps) OH NBE: HO Br O 65% yield Dalesconol A
4. Please provide a plausible mechanism for the following transformations and the structure of the isolable intermediate. (Org. Lett. 2016, 18, 3952−3955)
EtO2C O 1) ethyl diazoacetate LDA, THF, - 78 °C CsF OTMS 2) In(OTf)3, 4 A MS, CH2Cl2 N Boc H N TMS MeCN, reflux
