285124-04-1Relevant academic research and scientific papers
Stereoselective Synthesis of Functionalized Pyrrolidines by the Diverted N-H Insertion Reaction of Metallocarbenes with β-Aminoketone Derivatives
Nicolle, Simon M.,Lewis, William,Hayes, Christopher J.,Moody, Christopher J.
, p. 3749 - 3753 (2016)
A highly stereoselective route to functionalized pyrrolidines by the metal-catalyzed diverted N-H insertion of a range of diazocarbonyl compounds with β-aminoketone derivatives is described. A number of catalysts (rhodium(II) carboxylate dimers, copper(I) triflate, and an iron(III) porphyrin) are shown to promote the process under mild conditions to give a wide range of highly substituted proline derivatives. The reaction starts as a metallocarbene N-H insertion but is diverted by an intermolecular aldol reaction. The metal-catalyzed reaction of diazocarbonyl compounds with β-aminoketone derivatives leads to highly substituted pyrrolidines with excellent diastereoselectivity under mild reaction conditions. The reaction starts as a metallocarbene N-H insertion but is diverted by an intermolecular aldol reaction.
Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(iii) electrophile
Ding, Wei,Chai, Jinkui,Wang, Chen,Wu, Junliang,Yoshikai, Naohiko
, p. 8619 - 8624 (2020/06/05)
A method for the regio- and stereoselective synthesis of highly substituted vinyl ethers via trans-1,2-difunctionalization of alkynes with a cyclic λ3-iodane electrophile (benziodoxole triflate) and alcohols is reported. The reaction tolerates a variety of internal and terminal alkynes as well as various alcohols, affording β-λ3-iodanyl vinyl ethers in good yields with high regio- and stereoselectivities. The benziodoxole moiety of the products can be used as a versatile linchpin for the synthesis of structurally diverse vinyl ethers that are difficult to access by other means.
Three component synthesis of β-amino carbonyl compounds using indium trichloride-catalyzed one-pot Mannich-type reaction in water
Loh, Teck-Peng,Liung, Sarah B. K. W.,Tan, Kee-Leng,Wei, Lin-Li
, p. 3227 - 3237 (2007/10/03)
The use of indium trichloride as catalyst in a one-pot Mannich reaction in water gives high yields for the formation of β-aminoketones/esters/acids is described. The catalyst can be recycled when the reaction is complete (Loh T.-P.; Wei L.-L. Tetrahedron Lett. 1998, 39, 323). (C) 2000 Elsevier Science Ltd.
