172925-28-9Relevant academic research and scientific papers
Asymmetric total synthesis of cryptoconcatone I
Acharyya, Ranjan Kumar,Pal, Pratik,Chatterjee, Shrestha,Nanda, Samik
, p. 3552 - 3566 (2019)
Asymmetric total synthesis of the naturally occurring cryptoconcatone I, which possesses a γ-Z-butenolide framework, is described here for the first time. Asymmetric propargylation, E-selective cross metathesis, and regioselective reductive epoxide ring o
Enantioselective synthesis of propargylic alcohols by addition of enantiopure cyclopentadienyldialkoxyallyltitanium complexes to acetylenic aldehydes
BouzBouz, Samir,Pradaux, Fabienne,Cossy, Janine,Ferroud, Clotilde,Falguières, Annie
, p. 8877 - 8880 (2000)
The enantioselective synthesis of propargylic alcohols was achieved by enantioselective allyltitanation of acetylenic aldehydes. (C) 2000 Elsevier Science Ltd.
3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
Benaglia, Maurizio,Benincori, Tiziana,Raimondi, Laura Maria,Rossi, Sergio
, p. 535 - 546 (2020/03/27)
This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride), generate hypervalent silicon species that act as chiral Lewis acids in highly diastereo- and enantioselective organic reactions. Several relevant examples related to these applications are discussed in detail. 1 Introduction 2 The BITIOPO Family 3 Enantioselective Opening of Epoxides 4 Enantioselective Allylation of Aldehydes 5 Stereoselective Direct (Double) Aldol-Type Reaction with Ketones 6 Stereoselective Direct Aldol-Type Reaction with Ester Derivatives 7 Conclusions.
TetraPh-Tol-BITIOPO: A new atropisomeric 3,3′-bithiophene based phosphine oxide as an organocatalyst in Lewis base-catalyzed Lewis acid mediated reactions
Mirco, Abbinante Vincenzo,Maurizio, Benaglia,Sergio, Rossi,Tiziana, Benincori,Roberto, Cirilli,Marco, Pierini
supporting information, p. 7474 - 7481 (2019/08/20)
A new chiral phosphine oxide based on a 3,3′-bithiophene scaffold (TetraPh-Tol-BITIOPO) was synthesized, fully characterized and separated into antipodes through chiral HPLC. This new compound was successfully employed as an organocatalyst in Lewis base-catalyzed Lewis acid mediated reactions involving trichlorosilyl compounds. The new atropisomeric catalyst was able to promote the allylation of aldehydes with allyltrichlorosilane in up to 98% yield and up to 96% enantiomeric excess (ee), and the direct aldol reaction to afford β-hydroxy ketones and β-hydroxy thioesters, with good chemical yields and modest stereochemical efficiency. Computational studies helped to elucidate and to rationalize the stereochemical outcome of the reactions catalyzed by TetraPh-Tol-BITIOPO that was found to favour the formation of the isomer with an opposite absolute configuration in comparison with the products obtained with the previously reported 3,3′-bithiophene-based catalyst.
Axially chiral N,N′-dioxides ethers for catalysis in enantioselective allylation of aldehydes
Wu, Shijie,Xing, Yongfei,Wang, Jie,Guo, Xingchen,Zhu, Huajie,Li, Wan
supporting information, p. 947 - 957 (2019/08/30)
A series of axially chiral ethers synthesized from biscarboline N,N′-dioxides, (S)-1a to (S)-1n, was investigated in enantioselectivity addition reactions of allyltrichlorosilane with a series of substituted aldehydes, including bulky substituted aldehydes. High enantioselectivities (up to 96%ee) were achieved using the catalyst (S)-1k at 1 mol % loading.
Axial-Chiral Biisoquinoline N, N′-Dioxides Bearing Polar Aromatic C-H Bonds as Catalysts in Sakurai-Hosomi-Denmark Allylation
Reep, Carlyn,Morgante, Pierpaolo,Peverati, Roberto,Takenaka, Norito
supporting information, p. 5757 - 5761 (2018/09/29)
The design, synthesis, and evaluation of axial-chiral biisoquinolines bearing polar aromatic C-H bonds as Lewis base catalysts are reported. Lewis bases containing the 3,5-bis(trifluoromethyl)phenyl group were found to be significantly more enantioselecti
Chiral Unsymmetrically Substituted Bipyridine N,N′-Dioxides as Catalysts for the Allylation of Aldehydes
Ul?, Jan,Ne?as, David,Koukal, Petr,Havlí?ek, Vojtěch,To?ner, Zdeněk,Hybelbauerová, Simona,Kotora, Martin
supporting information, p. 5109 - 5116 (2018/07/31)
A series of unsymmetrically substituted diastereoisomeric (Ra,R) and (Sa,R) bipyridine N,N′-dioxides was synthesized by using oxidative coupling of the corresponding metallated tetrahydroisoquinoline N-oxides in the presence of iodin
Enantioselective Allyl-, and Allenylboration of Aldehydes Catalyzed by Chiral Hydroxyl Carboxylic Acid
Ota, Yuya,Kawato, Yuji,Egami, Hiromichi,Hamashima, Yoshitaka
supporting information, p. 976 - 980 (2017/05/05)
Asymmetric allylboration of aldehydes with allylboronic acid pinacol ester catalyzed by chiral hydroxyl carboxylic acid is described. This reaction provides synthetically useful homoallyl alcohols in high yield with good to high enantioselectivity. The pr
Asymmetric Allylation of Carbonyl Compounds Catalyzed by a Chiral Phosphine–Silver Complex
Yanagisawa, Akira,Yang, Nan,Bamba, Kentaro
supporting information, p. 6614 - 6618 (2017/12/15)
A catalytic, asymmetric allylation reaction of aldehydes or ketones with allyltrimethoxysilane was achieved by using a BINAP·AgBF4 [BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl] complex as the chiral precatalyst and triethylamine as the
A three-step total synthesis of goniothalesdiol A using a one-pot Sharpless epoxidation/regioselective epoxide ring-opening
Ramesh, Perla,Reddy, Yarram Narasimha
, p. 1037 - 1039 (2017/03/31)
Using a one-pot Sharpless asymmetric epoxidation/regioselective epoxide ring-opening as a key step, the protecting-group-free total synthesis of goniothalesdiol A was accomplished in only three steps starting from commercially available trans-cinnamaldehy
