1070-32-2Relevant academic research and scientific papers
Stereoselective conjugate addition of TMSI-activated butylcopper to 1-(R)-endo-(1-naphthyl)bornyl crotonate
Bergdahl, Mikael,Nilsson, Martin,Olsson, Thomas
, p. C19 - C22 (1990)
Conjugate addition of butylcopper/iodotrimethylsilane to naphthylbornyl crotonate (1) at -60 deg C gives 1-bornyl heptanoate (2) in 93percent yield and 98percent diastereomeric excess.The addition of TMSI-activated butylcopper is faster at -60 deg C than that of lithium dibutylcuprate (LiBu2Cu).
Cyclopropane intermediates in the synthesis of chiral alcohols with methyl-branched carbon skeleton. Application in the synthesis of insect pheromones
Kovalenko,Mineeva
, (2014)
Several chiral building blocks, (2R)-2-methylundec-10-en-1-ol, (3R)-3-methylheptan-1-ol, and (4R)-4-methyloctan-1-ol, have been synthesized using cyclopropane intermediate products. It has been shown that the obtained chiral alcohols can be used in the sy
Dispiroketals in synthesis (Part 16): Functionalised dispiroketals as new chiral auxiliaries; the synthesis of dihydroxylated dispiroketals in optically pure form and their application as bifunctional , C2-symmetrical, chiral auxiliaries for highly stereoselective Michael additions
Bezuidenhoudt, Barend C. B.,Castle, Grant H.,Innes, Jean E.,Ley, Steven V.
, p. 184 - 194 (1995)
A range of rigid, architecturally complex diols derived from dispiroketals have been synthesised.A bifunctional, C2-symmetrical, chiral auxiliary derived from these dihydroxylated dispiroketals has been used to induce a high degree of asymmetry in Michael additions of cuprates to a variety of di-α,β-unsaturated ester systems.
A New Asymmetric Synthesis of (S)-14-Methyloctadec-1-ene, the Sex Pheromone of the Peach Leafminer Moth
Bai, Hongjin,Du, Zhen-Ting,He, Guo-Guo,Liu, Lu,Tang, Meng,Wei, Liang,Zhang, Tao
, p. 1089 - 1095 (2020)
Abstract: An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of thepeach leafminer moth has been achieved. Based on the asymmetric methylation ofchiral (S)-4-benzyloxazolidin-2-one, thecarbon chain of the target molecule was assembled through aC1+C10+C4+C3procedure. The γ-lactone was transformed into 4-(benzyloxy)butanoic acid andthen, with the induction of Evan’s template, a chiral methyl group wasintroduced to the position of the carboxylic group in 97percent de. After reduction and a couple of chemicaloperations, the designed key intermediate A1was obtained. The synthesis of another moiety was started from decane-1,10-diolwhich was selectively protected and oxidized. The long carbon chain wasinstalled according to a Wittig protocol. After deprotection, oxidization, andmethylenation, the target molecule was synthesized in 7 linear steps with anoverall yield of 30.3percent.
Field and Electroantennogram Responses of the Pine Sawfly, Diprion nipponica, to Chiral Synthetic Pheromone Candidates
Tai, Akira,Higashiura, Yasutomo,Kakizaki, Masashi,Naito, Tikahiko,Tanaka, Kazuki,Fujita, Morifumi,Sugimura, Takashi,Hara, Hideho,Hayashi, Naotaka
, p. 607 - 608 (1998)
(1S, 2R, 6RS)-1,2,6-Trimethyldecyl propionate, a lower homolog of the sex pheromone of known sawflies, strongly attracted Diprion nipponica, a popular species in Japan.
Semiochemicals of the Scarabaeinae: VI. Identification of EAD-active constituents of abdominal secretion of male dung beetle, Kheper nigroaeneus.
Burger,Petersen
, p. 501 - 513 (2002)
Using gas chromatography with flame ionization detection (FID) and electroantennographic detection (EAD) in parallel, and employing chiral and achiral capillary columns, three constituents of the abdominal sex-attracting secretion of male Kheper nigroaeneus dung beetles were found to elicit reproducible EAD responses in male and female K. nigroaeneus antennae. One of these constituents is present in the secretion in such a small quantity that it could not be detected by FID, and it was not identified. The other constituents were identified as 3-methylindole (skatole) and (R)-(+)-3-methylheptanoic acid.
Lipase-catalyzed preparation of optically active isomers of cyclamen aldehyde
Kawasaki, Masashi,Goto, Michimasa,Hu, Dawei,Toyooka, Naoki,Kometani, Tadashi
, p. 27 - 33 (2013)
The optically active isomers of cyclamen aldehyde 1a were synthesized from a chiral intermediate prepared by lipase-catalyzed enantioselective transesterification of a prochiral diol with vinyl acetate. The absolute configuration of the enantiomer of 1a w
Cyclopropanol Methodology in the Synthesis of (4R)- and (4S)-4-Methyltetrahydro-2H-pyran-2-ones. Application in the Synthesis of Insect Pheromones with Methyl-Branched Carbon Skeleton
Mineeva
, p. 341 - 351 (2015)
A number of chiral methyl-branched building blocks have been synthesized starting from (4S)-4-methyltetrahydro-2H-pyran-2-one, and the possibility for using them for the preparation of mealworm beetle, rhinoceros beetle, and earth-boring dung beetle phero
Enantioselective Synthesis of the Sex Pheromone of Lichen Moth, Miltochrista calamine, and Its Diastereomer
Yuan, Gucheng,Liu, Jiawei,Yu, Shihang,Wang, Xueyang,Bian, Qinghua,Wang, Min,Zhong, Jiangchun
supporting information, p. 80 - 83 (2021/10/05)
The synthesis of a Miltochrista calamine sex pheromone and its diastereomer has been developed. The key steps of the synthetic approach involved Evans' chiral auxiliaries and the addition of alkyne to aldehyde, which were firstly applied to prepare this sex pheromone and its diastereomer. The synthetic sex pheromone could be used to trap insects and study physiological and ecological questions of the lichen moth.
Neutral iridium catalysts with chiral phosphine-carboxy ligands for asymmetric hydrogenation of unsaturated carboxylic acids
Yang, Shuang,Che, Wen,Wu, Hui-Ling,Zhu, Shou-Fei,Zhou, Qi-Lin
, p. 1977 - 1980 (2017/03/09)
We developed neutral iridium catalysts with chiral spiro phosphine-carboxy ligands (SpiroCAP) for asymmetric hydrogenation of unsaturated carboxylic acids. Different from the cationic Crabtree-type catalysts, the iridium catalysts with chiral spiro phosphine-carboxy ligands are neutral and do not require the use of a tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (BArF?) counterion, which is necessary for stabilizing cationic Crabtree-type catalysts. Another advantage of the neutral iridium catalysts is that they have high stability and have a long lifetime in air. The new iridium catalysts with chiral spiro phosphine-carboxy ligands exhibit unprecedented high enantioselectivity (up to 99.4% ee) in the asymmetric hydrogenations of various unsaturated carboxylic acids, particularly for 3-alkyl-3-methylenepropionic acids, which are challenging substrates for other chiral catalysts.
