133407-67-7Relevant academic research and scientific papers
One-pot oxidation and Wittig olefination of alcohols using o-iodoxybenzoic acid and stable Wittig ylide
Maiti,Yadav
, p. 1499 - 1506 (2001)
Benylic, allylic, and propargylic alcohols, as well as diols, can be oxidized with o-iodoxybenzoic acid (IBX) in the presence of stabilized Wittig ylide to generate α,β-unsaturated ester in one pot. This is useful when the intermediate aldehydes are unsta
γ-Butyrolactone, an Alternative Source of Chiral Iodo Derivatives.
Kermadec, Dominique,Prudhomme, Michelle
, p. 2757 - 2758 (1993)
An efficient synthesis of (3S) 1,3-di-tert-butyldimethylsilyloxy-6-iodohexane, a chiral iodo derivative useful for the preparation of functionalised 1,7-dioxaspiroundecanes from γ-butyrolactone is described.
Studies in tetrahydrofuran synthesis. Complete β-lactone formation in the bromolactonization of a 2,4-disubstituted β,γ-unsaturated carboxylic acid
Mead,Park
, p. 1205 - 1208 (1995)
A dienolate aldol/bromolactonization sequence has been used to demonstrate a new stereocontrolled route to protected α-(1-hydroxyalkyl) 2-oxetanones, and thus specifically functionalized tetrahydrofurans.
Cp*Rh(iii)/boron hybrid catalysis for directed C-H addition to β-substituted α,β-unsaturated carboxylic acids
Hirata, Yuki,Kojima, Masahiro,Matsunaga, Shigeki,Tanaka, Ryo,Yoshino, Tatsuhiko
, p. 76 - 79 (2021/12/29)
The C-H bond addition reaction of 2-phenylpyridine derivatives with α,β-unsaturated carboxylic acids catalyzed by Cp*Rh(iii)/BH3·SMe2is reported. Activation of C-H bonds with the rhodium catalyst and activation of α,β-unsaturated carboxylic acids with the boron catalyst cooperatively work, and a BINOL-urea hybrid ligand significantly improved the reactivity. With the optimized hybrid catalytic system, various β-disubstituted carboxylic acids were obtained under mild reaction conditions.
Gold-Catalyzed Asymmetric Thioallylation of Propiolates via Charge-Induced Thio-Claisen Rearrangement
Kim, Hanbyul,Jang, Jiwon,Shin, Seunghoon
, p. 20788 - 20795 (2020/11/27)
A gold(I)-catalyzed enantioselective thioallylation of propiolates with allyl sulfides is described. The key mechanistic element is a sulfonium-induced Claisen rearrangement which helps minimize the allyl dissociation and render higher enantioselectivity. This protocol features remarkable scope of the allyl moiety, allowing enantiocontrolled synthesis of all-carbon quaternary centers, and exhibits exceptional functional group compatibility with many Lewis bases and π-bonds. This intermolecular variant of Claisen rearrangement forges both C-S and C-C bonds concomitantly, providing efficient access to interesting optically active organosulfur compounds which can be transformed further through the vinyl sulfide as a functional handle. The rate of the reaction was zeroth order with respect to allyl sulfides, which suggested a reversible inhibition, providing a resting state for the catalyst. The Hammett plot displayed a correlation with σp values, suggesting a turnover-limiting sigmatropic rearrangement where decreased electron-density on sulfur accelerated the rearrangement.
First stereoselective total synthesis of paecilomycin G
Bujaranipalli, Sheshurao,Das, Saibal
, p. 2800 - 2802 (2016/06/09)
The stereoselective total synthesis of resorcylic acid lactone, paecilomycin G (1) has been accomplished. The key steps involved are the Corey-Fuchs reaction, Sharpless asymmetric dihydroxylation, Jacobsen hydrolytic kinetic resolution, Stille coupling, Mitsunobu reaction, and Ring-closing metathesis (RCM) reaction.
Stereoselective synthesis of dendrodolide-L
Bujaranipalli, Sheshurao,Das, Saibal
, p. 254 - 260 (2017/03/01)
An efficient stereoselective total synthesis of 12-membered macrolide dendrodolide L has been achieved. The key reactions involved are Keck asymmetric allylation, Jacobsen's hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, Mitsunobu reaction and ring-closing metathesis reaction.
A newly-designed PE-supported arsine for efficient and practical catalytic Wittig olefination
Wang, Peng,Liu, Chun-Rong,Sun, Xiu-Li,Chen, Shuai-Shuai,Li, Jun-Fang,Xie, Zuowei,Tang, Yong
supporting information; experimental part, p. 290 - 292 (2012/01/06)
A newly designed PE-supported arsine has been developed as an excellent catalyst for catalytic Wittig-type olefination. Simple ketones, in particular inactive ketones prove to be suitable substrates for the first time. This reaction provides an easy access to di-, tri-, and tetra-substituted olefins in high yield.
A practical total synthesis of (+)-spirolaxine methyl ether
Yadav,Sreenivas,Srinivas Reddy,Subba Reddy
supporting information; experimental part, p. 8307 - 8310 (2011/02/27)
An efficient and practical total synthesis of (+)-spirolaxine methyl ether is described. The phthalide-aldehyde 3 has been prepared via the Diels-Alder reaction between 1,4-unconjugated diene 5 and a long-chain acetylenic dienophile 6. The carbon framework of spiroketal sulfone 4 has been constructed from monobenzyl protected 1,5-pentanediol and the stereochemistry in both the phthalide portion and the spiroketal portion has been established by the Sharpless asymmetric epoxidation.
Studies towards the synthesis of the marine alkaloid chartelline C
Black, Phillip J.,Hecker, Evan A.,Magnus, Philip
, p. 6364 - 6367 (2008/02/12)
2,6-Dibromoindole 5 underwent regioselective Sonogashira coupling at the 2 position with simple acetylenic partners. While, imidazole-acetylene 16 failed to couple to 5, cyclic carbonate 19 succeeded to give 20, which was further elaborated into indole-imidazole 23.
