141540-20-7Relevant academic research and scientific papers
A selective C-H insertion/olefination protocol for the synthesis of α-methylene-γ-butyrolactone natural products
Lloyd, Matthew G.,D'Acunto, Mariantonietta,Taylor, Richard J. K.,Unsworth, William P.
supporting information, p. 1641 - 1645 (2016/02/09)
A regio- and stereoselective one-pot C-H insertion/olefination protocol has been developed for the late stage installation of α-methylene-γ-butyrolactones into conformationally restricted cyclohexanol-derivatives. The method has been successfully applied in the total synthesis of eudesmanolide natural product frameworks, including α-cyclocostunolide.
Diastereoselective synthesis of a highly functionalized cyclohexene embedded with a quaternary stereogenic centre by self Diels-Alder dimerization of a [3]dendralene attached to a (-)-menthol auxiliary
Singh, Rekha,Ghosh, Sunil K.
, p. 57 - 62 (2014/02/14)
A novel route to a chiral functionalized [3]dendralene attached to a (-)-menthol auxiliary has been developed, which involves a dimethylsulfonium methylide mediated olefination of a substituted ethenylidene phosphonoacetate (-)-menthyl ester, followed by
Lewis acid mediated asymmetric Diels-Alder reactions of chiral 2-phosphonoacrylates
Zhu, Jia-Liang,Chen, Po-Erh,Huang, Hue-Wen
, p. 23 - 36 (2013/02/23)
2-Phosphonoacrylates containing four chiral alcohol auxiliaries were efficiently prepared and evaluated in Lewis acid mediated Diels-Alder reactions. Under the activation of SnCl4, all reactions performed in CH 2Cl2 at -65 °C exclusively afforded the endo (endo-to-carboxylate) cycloadducts with dr's ranging from 50:50 to >99:1. The best facial selectivity was obtained from the substrate bearing a (-)-phenylmenthyl group, to give adducts as (dr >99:1) or almost as (dr = 99:1) single diastereomers. Detailed strategies for the structural elucidation of the cycloadducts as well as a rationalization of the observed stereoselectivity are described.
Chiral auxiliary based reductive alkylation of α, α-diallkyl β-phosphonyl esters
Bau, Jr-Sheng,Chen, I-Chia,Yang, Zhen-Xing,Zhu, Jia-Liang
, p. 531 - 541 (2013/07/27)
Acyclic α, α-disubstituted β-phosphonyl esters containing chiral alcoholic auxiliaries were efficiently prepared and evaluated for the lithium naphthalenide-mediated asymmetric reductive alkylation. Among which, the best diastereoselectivity was received fromthe substrates bearing a (-)-phenylmenthyl group in leading to alkylated esters with up to 83:17 dr. The diastereoselectivity is proven to be controlled by the π-facial differentiation created by the chiral ester as well as the geometry of tetrasubstituted enolates generated by the reductive cleavage of C-P bond.
Stereochemical considerations on the stereoselective cyclopropanation reactions of 3-aryl-2-phosphonoacrylates induced by the (-)-8-phenylmenthyl group as a chiral auxiliary
Takagi, Ryukichi,Hashizume, Miki,Nakamura, Minoru,Begum, Shahnaz,Hiraga, Yoshikazu,Kojima, Satoshi,Ohkata, Katsu
, p. 179 - 190 (2007/10/03)
The cyclopropanation of (-)-8-phenylmenthyl (E)-3-aryl-2-phosphonoacrylates E-3a-d with dimethyloxosulfonium methylide and diazomethane affords the corresponding trans cyclopropane derivatives as the major diastereomers with high diastereoselectivity. On
A Novel Type of Chiral Diphosphine Ligand, trans-2,3-Bis(diphenylphosphino)-1-methyl-1-cyclopropanecarboxylic Acid and Asymmetric Allylic Alkylation by the Use of Its Palladium Complex
Okada, Yoshiharu,Minami, Toru,Yamamoto, Tsutomu,Ichikawa, Junji
, p. 547 - 550 (2007/10/02)
Optically active trans-2,3-bis(diphenylphosphino)-1-methyl-1-cyclopropanecarboxylic acid was synthesized from trans-1,2-bis(diphenylphosphinyl)ethene via resolution of the racemic diphosphine oxide.Asymmetric allylic alkylation of 2-cyclohexenyl acetate w
