90719-27-0Relevant articles and documents
Silent catalytic promiscuity in the high-fidelity terpene cyclase δ-cadinene synthase
Loizzi, Marianna,Miller, David J.,Allemann, Rudolf K.
, p. 1206 - 1214 (2019/02/07)
δ-Cadinene synthase (DCS) is a high-fidelity sesquiterpene synthase that generates δ-cadinene as the sole detectable organic product from its natural substrate (E,E)-FDP. Previous work with this enzyme using substrate analogues revealed the ability of DCS
Asymmetric synthesis of isoquinuclidines by Diels-Alder reaction of 1,2-dihydropyridine utilizing a chiral Lewis acid catalyst
Seki, Chigusa,Hirama, Masafumi,Hutabarat, N.D.M. Romauli,Takada, Junko,Suttibut, Chonticha,Takahashi, Hideto,Takaguchi, Takuya,Kohari, Yoshihito,Nakano, Hiroto,Uwai, Koji,Takano, Nobuhiro,Yasui, Mitsukuni,Okuyama, Yuko,Takeshita, Mitsuhiro,Matsuyama, Haruo
experimental part, p. 1774 - 1781 (2012/03/10)
The chiral isoquinuclidine derivative, 2-azabicyclo[2.2.2]octane ring system, endo-(7R)-3 was obtained in good yield with excellent diastereoselectivity (up to 92% de) by Diels-Alder reaction of 1-(phenoxycarbonyl)-1,2-dihydropyridine 1 with N-acryloyl-(4S)-4- benzyloxazolidin-2-one (4S)-2 using titanium-(2R,3R)-TADDOLate 4 as a chiral Lewis acid catalyst in toluene at 0 °C. On the other hand, endo-(7S)-3 was obtained in good yield with excellent diastereoselectivity (up to 97% de) by Diels-Alder reaction of 1 with (4R)-2 using Cu(OTf)2/(4S,4′S)- bis(oxazoline) catalyst 8 as a chiral Lewis acid catalyst in dichloromethane at 0 °C. In these reactions, the choice of solvent and the combination of titanium-(2R,3R)-TADDOLate 4 {or Cu(II)/(4S,4′S)-bis(oxazoline) 8} and dienophile (4S)-2 {or (4R)-2} are very important. The stereochemistry of endo-(7R)-3 has been established to be (1R,4S,7R) and the reaction mechanism is proposed.
Diastereoselective aziridination of chiral electron-deficient olefins with N-chloro-N-sodiocarbamates catalyzed by chiral quaternary ammonium salts
Murakami, Yuta,Takeda, Youhei,Minakata, Satoshi
experimental part, p. 6277 - 6285 (2011/10/02)
Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the