175410-79-4Relevant academic research and scientific papers
Synthesis of Weinreb amides using diboronic acid anhydride-catalyzed dehydrative amidation of carboxylic acids
Shimada, Naoyuki,Takahashi, Naoya,Ohse, Naoki,Koshizuka, Masayoshi,Makino, Kazuishi
supporting information, p. 13145 - 13148 (2020/11/09)
The first successful example of the direct synthesis of Weinreb amides using catalytic hydroxy-directed dehydrative amidation of carboxylic acids using the diboronic acid anhydride catalyst is described. The methodology is applicable to the concise syntheses of eight α-hydroxyketone natural products, namely, sattabacin, 4-hydroxy sattabacin, kurasoins A and B, soraphinols A and B, and circumcins B and C.
Utilization of whole cell mediated deracemization in a chemoenzymatic synthesis of enantiomerically enriched polycyclic chromeno[4,3-b] pyrrolidines
Saravanan, Thangavelu,Jana, Sushital,Chadha, Anju
supporting information, p. 4682 - 4690 (2014/06/24)
Various aryl and alkyl substituted optically pure propargyl alcohols were obtained with excellent ee (up to >99%) and isolated yields (up to 87%) by deracemization using whole cells of Candida parapsilosis ATCC 7330. The whole cells show substrate specificity towards alkyl substituted propargyl alcohols and a switch in the enantioselectivity has been observed from 'R' to 'S' upon increasing the chain length. For the first time, enantiopure (R)-4-(3-hydroxybut-1-ynyl)benzonitrile, (R)-4-(biphenyl-4-yl)but-3-yn-2-ol, (S)-ethyl 3-hydroxy-5-phenylpent-4-ynoate and (S)-4-phenylbut-3-yne-1,2-diol were obtained using this strategy. Optically pure propargyl alcohol thus obtained was used as a chiral starting material in the synthesis of enantiomerically enriched poly-substituted pyrrolidines and a pyrrole derivative successfully demonstrating a chemoenzymatic route. This journal is
A Bronsted acid mediated cascade enone synthesis from aldehydes containing a tethered propargylsilane
Ramalho, Rui,Jervis, Peter J.,Kariuki, Benson M.,Humphries, Alexander C.,Cox, Liam R.
, p. 1631 - 1634 (2008/09/17)
(Chemical Equation Presented) MeSO3H effects the intramolecular allenylation of a series of aldehydes 1 to provide allenyl alcohol product 3 as a single diastereoisomer. Cyclization proceeds rapidly at -78°C. However, when the reaction is perfo
Synthesis of alkylidenecyclopentenones and dialkylidenecyclopentenones via the coupling of propargylic alcohol and 2-alkyne-1,4-diol derivatives with cyclopropylcarbene-chromium complexes
Herndon, James W.,Zhu, Jin,Sampedro, Diego
, p. 4985 - 4993 (2007/10/03)
The coupling of propargylic alcohols and their derivatives with cyclopropylcarbene-chromium complexes has been investigated. The coupling reaction leads to alkylidenecyclopentenones or alkoxyalkyl-cyclopentenones, depending on the leaving group ability of
Synthesis of alkylidenecyclopentenones via the coupling of propargyl alcohol derivatives with cyclopropylcarbene-chromium complexes
Herndon, James W.,Zhu, Jin
, p. 15 - 18 (2008/02/09)
(equatio presented) The coupling of propargylic alcohols and their derivatives with cyclopropylcarbene-chromium complexes has been investigated. The coupling reaction leads to alkylidenecyclopentenones or alkoxyalkylcyclopentenones, depending on the leavi
Chiral bipyrindine and biquinoline ligands: Their asymmetric synthesis and application to the synthesis of trans-whisky lactone
Ito, Katsuji,Yoshitake, Miwa,Katsuki, Tsutomu
, p. 3905 - 3920 (2007/10/03)
Chiral bipyrindine and biquinoline which have been reported to be efficient ligands for the construction of chiral copper catalysts, were synthesized enantioselectively by using Mn-salen catalyzed asymmetric epoxidation as a key step. Enantioselective synthesis of trans-whisky lactone was then achieved by way of enantiospecific ring expansion reaction of oxetane with a chiral copper catalysts bearing the bipyrindine ligand as a chiral source.
