Supramolecular Control of Photocycloadditions in Solution: In Situ Stereoselective Synthesis and Release of Cyclobutanes

2019 ◽  
Vol 131 (12) ◽  
pp. 4026-4031 ◽  
Author(s):  
Li‐Li Ma ◽  
Yuan‐Yuan An ◽  
Li‐Ying Sun ◽  
Yao‐Yu Wang ◽  
F. Ekkehardt Hahn ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Supramolecular Control

Supramolecular Control of Photocycloadditions in Solution: In Situ Stereoselective Synthesis and Release of Cyclobutanes

2019 ◽  
Vol 58 (12) ◽  
pp. 3986-3991 ◽  
Author(s):  
Li‐Li Ma ◽  
Yuan‐Yuan An ◽  
Li‐Ying Sun ◽  
Yao‐Yu Wang ◽  
F. Ekkehardt Hahn ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Supramolecular Control

A Metal-free and β-Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides: Synthesis of 5-aza analogues of Aquayamycin

Synlett ◽  
2021 ◽  
Author(s):  
Yuling Mei ◽  
nan jiang ◽  
Yu Yang ◽  
Wan Zhang ◽  
Saifeng Qiu ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Metal Free ◽  
Wide Range ◽  
One Step ◽  
Aryl Glycosides ◽  
Aryl Glycoside

A convenient protocol for β-stereoselective synthesis of 2-deoxy-C-aryl glycosides has been developed. This reaction takes place in one step by using I2/Et3SiH to activate glycosyl acetate to generate glycosyl iodide intermediate in situ, which was captured by naphthol followed by Fries-like O- → C-glycoside rearrangement to selectively afford β-C-aryl glycoside. The approach is applicable to a wide range of naphthol modules, and its utility was demonstrated in the synthesis of 5-aza analogues of Aquayamycin.

scholarly journals Ru-catalyzed isomerization of ω-alkenylboronates towards stereoselective synthesis of vinylboronates with subsequent in situ functionalization

2020 ◽  
Vol 11 (23) ◽  
pp. 5944-5949 ◽  
Author(s):  
Guo-Ming Ho ◽  
Lucas Segura ◽  
Ilan Marek
Keyword(s):  
Stereoselective Synthesis ◽  
In Situ Functionalization

A regio- and stereoselective ruthenium-catalyzed isomerization of ω-alkenyl boronates into stereodefined di- and trisubstituted alkenylboronate derivatives is reported.

Unprecedented One-Pot Stereoselective Synthesis of Knoevenagel-Type Derivatives­ via in situ Condensation of N-Methyleniminium Salts of Ethylenethiourea­ and Ethyleneurea with Active Methylene Reagents

Synthesis ◽  
2007 ◽  
Vol 2007 (16) ◽  
pp. 2495-2502 ◽  
Author(s):  
Angelo Ranise ◽  
Sara Cesarini ◽  
Andrea Spallarossa ◽  
Fernando Sancassan ◽  
Francesco Bondavalli ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
One Pot ◽  
Active Methylene

An efficient [4+3] cycloaddition reaction of aza-o-quinodimethanes with C,N-cyclic azomethine imines: stereoselective synthesis of 1,2,4-triazepines

RSC Advances ◽  
2015 ◽  
Vol 5 (94) ◽  
pp. 76696-76699 ◽  
Author(s):  
L. Chen ◽  
G. M. Yang ◽  
J. Wang ◽  
Q. F. Jia ◽  
J. Wei ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Cycloaddition Reaction ◽  
Azomethine Imines

An efficient [4+3] cycloaddition reaction of in situ generated aza-o-quinodimethanes with C,N-cyclic azomethine imines has been developed.

Stereoselective Synthesis of (Z)-Allyl Alcohols through Coinage-Metal-Catalyzed Nucleophilic Addition of Benzo[d]isoxazoles with Unactivated Propargyl Alcohols

Synlett ◽  
2019 ◽  
Vol 30 (11) ◽  
pp. 1339-1345
Author(s):  
Zhiyuan Chen ◽  
Wenjin Wu ◽  
Tiantian Zheng ◽  
Jie Tan ◽  
Shouzhi Pu
Keyword(s):  
Stereoselective Synthesis ◽  
Silver Salt ◽  
Gold Catalyst ◽  
Building Blocks ◽  
Coinage Metal ◽  
Stereoselective Addition ◽  
Allyl Alcohols ◽  
Metal Catalyzed ◽  
Propargyl Alcohols

The Au/Ag-cocatalyzed stereoselective addition reaction of cyanophenol anion species generated in situ with unactivated propargyl alcohols to produce functionalized (Z)-allyl alcohols in mostly good yields is reported. Benzo[d]isoxazoles were found to be excellent building blocks for the production of highly reactive cyanophenol anions from Kemp elimination reactions, thus serving as a masked benzonitrile source for the preparation of organonitrile derivatives. Silver salt combined with gold catalyst were found to be necessary for the success of this transformation.

Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified Ramberg–Bäcklund reaction

2004 ◽  
Vol 82 (5) ◽  
pp. 622-630 ◽  
Author(s):  
Yang Li ◽  
Yu Zhang ◽  
Zhi Huang ◽  
Xiaoping Cao ◽  
Kun Gao
Keyword(s):  
Potassium Hydroxide ◽  
Stereoselective Synthesis ◽  
Starting Material ◽  
Mitsunobu Reaction ◽  
Dichloromethane Solution ◽  
Naturally Occurring

A convenient and rapid approach for the synthesis of naturally occurring unsaturated amide alkaloids 1a–1n by the recently developed one-flask Ramberg–Bäcklund reaction is described. The starting material was alcohol 3, which was transformed into thiolacetate 4 using the Mitsunobu reaction. In situ cleavage of acetyl moiety of 4, followed by alkylation of the resulting thiol with appropriate chloroacetamide 5, provided the sulfide 6. Oxidation of sulfide 6 gave the corresponding sulfone 2. Treatment of the sulfone 2 with the dibromodifluoromethane in the presence of alumina-supported potassium hydroxide in dichloromethane solution afforded unsaturated amide alkaloids 1a–1n. To the best of our knowledge, the synthesis of 1e and 1i was reported for the first time.Key words: synthesis, unsaturated amide alkaloids, Ramberg–Bäcklund reaction.

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