29430-66-8Relevant articles and documents
One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping
Yamane, Daichi,Tanaka, Haruna,Hirata, Akihiro,Tamura, Yumiko,Takahashi, Daichi,Takahashi, Yusuke,Nagamitsu, Tohru,Ohtawa, Masaki
supporting information, p. 2831 - 2835 (2021/05/05)
A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.
Palladium-Catalyzed One-Pot Conversion of Aldehydes and Ketones into 4-Substituted Homopropargyl Alcohols and 5-En-3-yn-1-ols ?
Umana, Christian A.,Cabezas, Jorge A.
, p. 9505 - 9514 (2017/09/23)
Sequential treatment of 2,3-dichloropropene with magnesium and n-BuLi generated the equivalent of 1,3-dilithiopropyne, which adds regiospecifically to aldehydes and ketones to produce homopropargyl alcohols. The lithium acetylide intermediate formed in this protocol can be further reacted with aromatic and vinyl halides, under palladium catalysis, to produce 4-substituted homopropargyl alcohols and 5-en-3-yn-1-ols, respectively, in one-pot with good overall yields.
Electrophilic cyclization and intermolecular acetalation of 2-(4- hydroxybut-1-yn-1-yl)benzaldehydes: Synthesis of diiodinated diepoxydibenzo[c,k][1,9]dioxacyclohexadecines
Wang, Jia,Zhu, Hai-Tao,Chen, Si,Luan, Cheng,Xia, Yu,Shen, Yi,Li, Ying-Xiu,Hua, Yingxi,Liang, Yong-Min
, p. 10641 - 10649 (2018/05/31)
An expedient strategy for the preparation of diiodinated diepoxydibenzo[c,k][1,9]dioxacyclohexadecines from readily available 2-(4-hydroxybut-1-yn-1-yl)- benzaldehydes through electrophile-triggered tandem cyclization/ intermolecular acetalation sequence