Facile and Efficient Synthesis of Lactols by a Domino Reaction of 2,3-Epoxy Alcohols with a Hypervalent Iodine(III) Reagent and Its Application to the Synthesis of Lactones and the Asymmetric Synthesis of (+)-Tanikolide

2007 ◽  
Vol 13 (18) ◽  
pp. 5238-5248 ◽  
Author(s):  
Hiromichi Fujioka ◽  
Satoshi Matsuda ◽  
Mai Horai ◽  
Eri Fujii ◽  
Maiko Morishita ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Domino Reaction ◽  
Hypervalent Iodine ◽  
Efficient Synthesis ◽  
Epoxy Alcohols

Hypervalent Iodine Oxidation ofp-Alkoxy- and Related Phenols: A Facile and Efficient Synthesis ofp-Quinones

Synthesis ◽  
1989 ◽  
Vol 1989 (02) ◽  
pp. 126-127 ◽  
Author(s):  
Yasumitsu Tamura ◽  
Takayuki Yakura ◽  
Hirofumi Tohma ◽  
Kazumi Ki-kuchi ◽  
Yasuyuki Kita
Keyword(s):  
Hypervalent Iodine ◽  
Efficient Synthesis

Asymmetric Synthesis of 2,3,6-Trisubstituted Piperidines via Baylis–Hillman Adducts and Lithium Amide through Domino Reaction

Synlett ◽  
2019 ◽  
Vol 31 (06) ◽  
pp. 600-604 ◽  
Author(s):  
Mateo M. Salgado ◽  
Alejandro Manchado ◽  
Carlos T. Nieto ◽  
David Díez ◽  
Narciso M. Garrido
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Claisen Rearrangement ◽  
Domino Reaction ◽  
Amino Acid Derivative ◽  
Side Chain ◽  
Lithium Amide ◽  
Stereochemical Control ◽  
Asymmetric Michael Addition ◽  
Polysubstituted Piperidines

A convenient asymmetric synthesis of methyl (2S,3S,6R)-6-(4-fluorophenyl)-2-(4-hydroxyphenyl)-piperidine-3-carboxylate is described, starting from Baylis–Hillman adducts. The route involves a domino process: allylic acetate rearrangement, stereoselective Ireland–Claisen rearrangement and asymmetric Michael addition, which provides a δ-amino acid derivative with full stereochemical control. A subsequent chemoselective transformation of one of the side-chain groups allows an effective cyclization leading to biologically interesting polysubstituted piperidines in which the 2,6-aryl groups could be attached sequentially.

scholarly journals Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

2019 ◽  
Vol 15 ◽  
pp. 874-880
Author(s):  
Razieh Navari ◽  
Saeed Balalaie ◽  
Saber Mehrparvar ◽  
Fatemeh Darvish ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Room Temperature ◽  
High Selectivity ◽  
Domino Reaction ◽  
Primary Amines ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Efficient Approach ◽  
Three Component Reaction ◽  
High Yields

An efficient approach for the synthesis of pyrazolopyridines containing the aminochromane motif through a base-catalyzed cyclization reaction is reported. The synthesis was carried out through a three-component reaction of (arylhydrazono)methyl-4H-chromen-4-one, malononitrile, primary amines in the presence of Et3N at room temperature. However, carrying out the reaction under the same conditions without base led to a fused chromanyl-cyanopyridine. High selectivity, high atom economy, and good to high yields in addition to mild reaction conditions are the advantages of this approach.

ChemInform Abstract: Efficient Synthesis of Quinoxalines with Hypervalent Iodine as a Catalyst.

ChemInform ◽  
2014 ◽  
Vol 45 (11) ◽  
pp. no-no
Author(s):  
Chung-Yu Chen ◽  
Wan-Ping Hu ◽  
Mei-Chun Liu ◽  
Pi-Cheng Yan ◽  
Jeh-Jeng Wang ◽  
...  
Keyword(s):  
Hypervalent Iodine ◽  
Efficient Synthesis

A Concise and Modular Three-Step Synthesis of (S)-Verapamil using an Enantioselective Rhodium-Catalyzed Allylic Alkylation Reaction

Synthesis ◽  
2020 ◽  
Vol 52 (15) ◽  
pp. 2185-2189 ◽  
Author(s):  
P. Andrew Evans ◽  
Mai-Jan Tom ◽  
Ben W. H. Turnbull
Keyword(s):  
Calcium Channel ◽  
Asymmetric Synthesis ◽  
Channel Blocker ◽  
Alkylation Reaction ◽  
Allylic Alkylation ◽  
Efficient Synthesis ◽  
Terminal Olefin ◽  
Bioactive Agents ◽  
Quaternary Stereocenter ◽  
Modular Nature

A concise and modular asymmetric synthesis of the calcium channel blocker (S)-verapamil is described. This approach employs an enantioselective rhodium-catalyzed allylic alkylation reaction between an α-isopropyl-substituted benzylic nitrile and allyl benzoate to construct the challenging acyclic quaternary stereocenter. The terminal olefin then serves as a convenient synthetic handle for a hydroamination to introduce the phenethylamine moiety, furnishing (S)-verapamil in three steps and 55% overall yield, thus providing the most efficient synthesis of this important pharmaceutical reported to date. Furthermore, given the modular nature of the synthesis, it can be readily modified to prepare structurally related bioactive agents.

Sign in / Sign up

Export Citation Format

Share Document