10348-08-0Relevant articles and documents
Nucleo-Palladation-Triggering Alkene Functionalization: A Route to γ-Lactones
Zheng, Meifang,Chen, Pengquan,Huang, Liangbin,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 5756 - 5759 (2017/11/10)
An unprecedented strategy for the highly effective synthesis of γ-lactones from homoallylic alcohols was achieved by palladium catalysis in one step. The protocol affords aryl, alkyl, and spiro γ-lactones directly from readily available homoallylic alcohols in good yields with excellent functional group tolerance and high chemoselectivity under mild conditions.
MnO2-promoted carboesterification of alkenes with anhydrides: A facile approach to γ-lactones
Wu, Lihuan,Zhang, Zhenming,Liao, Jianhua,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 2628 - 2631 (2016/02/18)
An efficient carboesterification of alkenes with anhydrides promoted by MnO2 has been developed to afford functionalized γ-lactones in good to excellent yields. This method shows a broad substrate scope and provides a valuable and convenient synthetic tool for constructing γ-lactones.
Synthesis of Lactones via C-H Functionalization of Nonactivated C(sp3)-H Bonds
Richers, Johannes,Heilmann, Michael,Drees, Markus,Tiefenbacher, Konrad
, p. 6472 - 6475 (2016/12/23)
An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp3)-H bonds through radical 1,5-hydrogen abstraction. The γ-bromoamides formed are subsequently converted to γ-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp3-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of γ-lactones into complex carbon frameworks.
A new synthesis of γ-butyrolactones via AuCl3- or Hg(II)-catalyzed intramolecular hydroalkoxylation of 4-bromo-3-yn-1-ols
Reddy, Maddi Sridhar,Kumar, Yalla Kiran,Thirupathi, Nuligonda
, p. 824 - 827 (2012/04/05)
An efficient conversion of 4-bromo-3-yn-1-ols to γ-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.
Direct lactone formation by using hypervalent iodine(III) reagents with KBr via selective C-H abstraction protocol
Dohi, Toshifumi,Takenaga, Naoko,Goto, Akihiro,Maruyama, Akinobu,Kita, Yasuyuki
, p. 3129 - 3132 (2008/02/09)
We have developed a new and reliable method for the direct construction of biologically important aryl lactones and phthalides from carboxylic and benzoic acids, using a combination of hypervalent iodine(III) reagents with KBr.
An analysis of the factors contributing to the regioselectivity observed in the opening of oxiranes
Kayser, Margaret M.,Morand, Peter
, p. 302 - 306 (2007/10/02)
The regioselectivity of epoxide ring opening can be analyzed in terms of hard-soft acid base (HSAB) theory.The coordination of the hard acid with the oxigen atom of the oxirane ring produces a "pulling effect" which determines the direction of the ring opening.In the absence of strong "pulling effect" the "pushing effect" of the approaching base is examined and the consequences of relative softness or hardness of the nucleophile on the regioselectivity of the ring opening are discussed.
