1072028-48-8Relevant articles and documents
Stereoselective Total Synthesis of (-)-(2 S,4 R)-3′-Methoxyl Citreochlorol: Preparation and Use of New Proline-Based Auxiliary for Asymmetric Acetate Aldol Reaction
Sunnapu, Ranganayakulu,Banoth, Saikumar Naik,Reyno,Thomas, Aleena,Venugopal, Navyasree,Rajendar, Goreti
, p. 4103 - 4113 (2020/03/05)
The first stereoselective total synthesis of (-)-(2S,4R)-3′-methoxy citreochlorol and (-)-(2S,4S)-3′-methoxy citreochlorol is demonstrated. A proline-based imidazolidinone was synthesized and used as chiral auxiliary for asymmetric acetate aldol reaction to generate initial chirality in the targeted molecule. Geminal dichloromethane functionality was introduced by the addition of in situ generated dichloromethyllithium to Weinreb's amide functional group.
Novel diarylprolinol-derived amino perfluoroalkanesulfonamide catalysts: Highly Enantio- and diastereoselective aldol reaction
Lutete, Léopold M.,Ikemoto, Tetsuya
supporting information, p. 577 - 579 (2017/04/03)
A new series of amino perfluoroalkanesulfonamide compounds derived from diarylprolinols has been developed and found to be efficient catalysts for the reaction of ethyl glyoxylate with 4-(benzyloxy)butanal. The aldol product, obtained in good yield with excellent enantio- and diastereomeric excess, is an intermediate for the synthesis of bis-THF alcohol, which is a commonly used unit in the design of HIV protease inhibitors such as Darunavir.
Synthesis of chiral 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine and their application to enantioselective borane reduction of prochiral ketones as chiral catalysts
Hosoda, Naoya,Kamito, Hideaki,Takano, Miki,Takebe, Yoshitaka,Yamaguchi, Yoshitaka,Asami, Masatoshi
, p. 1739 - 1746 (2013/03/13)
Chiral diamines, 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine, were prepared from N-(tert-butoxycarbonyl) pyrrolidine or (S)-proline as a starting material, respectively. These chiral diamines were efficient for the catalytic enantioselective borane reduction of acetophenone. Using (S)-2-(anilinodiphenylmethyl)pyrrolidine, chiral secondary alcohols were obtained from prochiral ketones with good to excellent enantiomeric excesses (up to 98% ee).